Organic light-emitting devices

Abstract

The present specification provides an organic light-emitting device, which includes: an anode; a cathode arranged to face the anode; a light-emitting layer arranged between the anode and the cathode; a first organic material layer arranged between the anode and the light-emitting layer; and a second organic material layer arranged between the cathode and the light-emitting layer, wherein among the organic materials contained in the light-emitting layer and the organic material layer, the band gap energy (E bg ) is 3 eV or greater, the first organic material layer contains one or more compounds each centered on an sp3 carbon, the second organic material layer contains one or more compounds each centered on an sp3 carbon, and the first organic material layer and the second organic material layer contain three or more compounds each centered on an sp3 carbon.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0135216, filed on November 6, 2018, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to organic light emitting devices. Background Art

[0003] The organic light emitting device has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined with each other in the organic thin film to form pairs, and then the paired electrons and holes emit light while annihilating. The organic thin film may be composed of a single layer or multiple layers as needed.

[0004] Efforts are constantly being made to improve the external quantum efficiency (EQE) of each of the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer of an organic light-emitting device. As an example of such efforts, the red light-emitting layer and the green light-emitting layer each contain a phosphorescent material, and in particular, phosphorescent materials using Ir complexes have been actively studied, and efforts to introduce phosphorescent materials into the blue light-emitting layer are also continuing, but the development of blue hosts requiring high singlet energy and triplet energy is currently at a low level.

[0005] In addition, since the blue light-emitting layer emits higher energy than the red light-emitting layer and the green light-emitting layer and shows a tendency to be greatly affected by the durability of organic materials and the damage to other organic materials according to the light-emitting area in the light-emitting layer, it is necessary to develop a stable organic light-emitting device with excellent efficiency, performance and service life. Summary of the invention

[0006] Technical issues

[0007] The present specification provides an organic light emitting device having low driving voltage, high efficiency, and long lifespan characteristics.

[0008] Technical Solution

[0009] The present invention is directed to providing an organic light-emitting device, the organic light-emitting device comprising: an anode; a cathode disposed to face the anode; a light-emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the anode and the light-emitting layer; and a second organic material layer disposed between the cathode and the light-emitting layer, wherein among the organic materials contained in the light-emitting layer, the first organic material layer, and the second organic material layer, the band gap energy (E bg) are each 3 eV or greater, the first organic material layer contains one or more compounds each centered on an sp3 carbon, the second organic material layer contains one or more compounds each centered on an sp3 carbon, and the first organic material layer and the second organic material layer contain three or more compounds centered on an sp3 carbon.

[0010] Beneficial Effects

[0011] Since the organic light-emitting device of the present invention smoothly injects and transports carriers in each layer by including three or more compounds each centered on sp3 carbon in a first organic material layer arranged between the anode and the light-emitting layer and a second organic material layer arranged between the cathode and the light-emitting layer, it is possible to achieve carrier balance of the device and improve the service life of the device by improving the electrochemical durability of the compounds centered on sp3 carbon.

[0012] In addition, due to the band gap energy (E bg ) is 3 eV or greater, so the organic light-emitting device has the effect of increasing the service life by improving the durability of the organic light-emitting device and improving the overall efficiency of the device by avoiding the diffusion and energy transfer of excitons.

[0013] Since the compatibility of organic light-emitting devices is established, it can be observed that the combination of each compound applied to each organic material layer can produce a large difference in the overall performance of the device. The present invention smoothly injects and transports carriers injected from each electrode and achieves balance in the light-emitting layer by including a total of three or more compounds each composed of sp3 carbon as the center in the region of 1) an organic material layer disposed between the anode and the light-emitting layer and 2) an organic material layer disposed between the cathode and the light-emitting layer. In addition, the service life of the device can be improved by improving the electrochemical durability of the compound composed of sp3 carbon at the center. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8 and a cathode 9 is shown.

[0015] Figure 2 An example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 10, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8 and a cathode 9 is shown.

[0016] [Explanation of Reference Numerals]

[0017] 1: Base

[0018] 2: Anode

[0019] 3: Hole injection layer

[0020] 4: Hole transport layer

[0021] 5: Luminous layer

[0022] 6: Hole blocking layer

[0023] 7: Electron transport layer

[0024] 8: Electron injection layer

[0025] 9: Cathode

[0026] 10: Electron blocking layer DETAILED DESCRIPTION

[0027] Hereinafter, the present specification will be described in more detail.

[0028] The organic light emitting device of the present invention comprises: an anode; a cathode arranged to face the anode; a light emitting layer arranged between the anode and the cathode; a first organic material layer arranged between the anode and the light emitting layer; and a second organic material layer arranged between the cathode and the light emitting layer, wherein among the organic materials contained in the light emitting layer, the first organic material layer and the second organic material layer, the band gap energy (E bg ) is 3 eV or greater, the first organic material layer contains one or more compounds each centered on an sp3 carbon, the second organic material layer contains one or more compounds each centered on an sp3 carbon, and the first organic material layer and the second organic material layer contain three or more compounds each centered on an sp3 carbon.

[0029] In an exemplary embodiment of the present specification, among the organic materials included in the organic material layer of the organic light-emitting device, the band gap energy (E bg ) may each be 3 eV or more, preferably each be 3 eV or more and 4 eV or less.

[0030] In an exemplary embodiment of the present specification, the dopant compound means a compound added in a small amount in each organic material layer, and specific examples thereof include a light-emitting dopant of the light-emitting layer and a p-dopant of the hole injection layer, but are not limited thereto. The dopant compound may be contained in each organic material layer in an amount of 0.1 wt % to 20 wt %, preferably 0.1 wt % to 10 wt %.

[0031] Band gap energy (Ebg ) can be obtained by measuring the LUMO energy and HOMO energy of a molecule.

[0032] In order to understand the distribution of electrons in molecules and optical properties, a definite structure is required. In addition, the electronic structure has different structures in neutral state, anionic state and cationic state according to the charge state of the molecule. In order to drive the device, all energy levels in neutral state, cationic state and anionic state are important, and the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the neutral state are representatively considered as important characteristics.

[0033] In order to determine the molecular structure of chemical materials, the structure of input is optimized using density functional theory. In order to calculate DFT, the BPW91 calculation method (Becke exchange and Perdew correlation-correlation function) and the dual numerical basis set (DNP) basis set including polarization function are used. The BPW91 calculation method is published in the paper "AD Becke, Phys. Rev. A, 38, 3098 (1988)" and "JP Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992)", and the DNP basis set is published in the paper "B. Delley, J. Chem. Phys., 92, 508 (1990)".

[0034] In order to perform calculations by density functional theory, a "DMol3" software package manufactured by BIOVIA Dassault Systèmes can be used. When the optimal molecular structure is determined using a given method, energy levels that can be occupied by electrons can be obtained as a result. HOMO energy refers to the orbital energy at the highest energy level in a molecular orbital filled with electrons when the energy in a neutral state is obtained, and LUMO energy refers to the orbital energy at the lowest energy level in a molecular orbital not filled with electrons.

[0035] In the present invention, "a compound having an sp3 carbon as the center" means a compound having a core structure having an sp3 carbon as the center.

[0036] Specifically, a compound composed of sp3 carbon as the center means a compound whose core structure is formed by sp3 carbon at the center as in the compound represented by the following formula 1, and a compound in which a core structure not containing sp3 carbon is bonded to a substituent containing sp3 carbon does not mean a compound composed of sp3 carbon as the center.

[0037] [Formula 1]

[0038]

[0039] According to an exemplary embodiment of the present invention, the first organic material layer and the second organic material layer include a total of three or more compounds each centered on sp3 carbon. According to another exemplary embodiment, the first organic material layer and the second organic material layer may include a total of three to twenty, specifically three to ten, more specifically three to six compounds each centered on sp3 carbon, but is not limited thereto.

[0040] Since this achieves a balance in carriers injected from both electrodes, there is an advantage that when the compound is applied to a device, the service life of the device is improved.

[0041] The first organic material layer may be one or more selected from the following: a hole transport layer, a hole injection layer, a layer that simultaneously transports and injects holes, and an electron blocking layer, and one or more of the first organic material layers contain a compound composed of sp3 carbon as the center.

[0042] According to an exemplary embodiment of the present invention, the first organic material layer including the compound composed of sp3 carbon as the center may be one or more of: a hole transport layer, a hole injection layer, and an electron blocking layer, but is not limited thereto.

[0043] The second organic material layer may be one or more selected from the following: an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer, and one or more of the second organic material layers contain a compound composed of sp3 carbon as the center.

[0044] According to an exemplary embodiment of the present invention, the second organic material layer including the compound composed of sp3 carbon as the center may be one or more of: an electron transport layer, an electron injection layer, and a hole blocking layer, but is not limited thereto.

[0045] According to an exemplary embodiment of the present invention, in an organic light-emitting device, one or more layers in the first organic material layer contain one or more compounds each centered on an sp3 carbon, wherein the sp3 carbon-centered compound contains a substituted or unsubstituted amine group, and one or more layers in the second organic material layer contain one or more compounds each centered on an sp3 carbon, wherein the sp3 carbon-centered compound contains a substituted or unsubstituted nitrogen-containing aromatic 5-membered ring, a substituted or unsubstituted nitrogen-containing aromatic 6-membered ring, or a substituted or unsubstituted nitrogen-containing aromatic polycyclic ring.

[0046] One or more layers in the second organic material layer contain one or more compounds in which a core structure composed of sp3 carbon at the center is substituted with a substituted or unsubstituted nitrogen-containing aromatic 5-membered ring, a substituted or unsubstituted nitrogen-containing aromatic 6-membered ring, or a substituted or unsubstituted nitrogen-containing aromatic polycyclic ring.

[0047] According to an exemplary embodiment of the present invention, "a substituted or unsubstituted nitrogen-containing aromatic 5-membered ring, a substituted or unsubstituted nitrogen-containing aromatic 6-membered ring, or a substituted or unsubstituted nitrogen-containing aromatic polycyclic ring" may be represented by the following formula B. Specifically, the core structure represented by Formula 1 may be substituted with the following formula B.

[0048] [Formula B]

[0049] *-(L11)n-Ar11

[0050] In formula B,

[0051] * means the position to be bonded,

[0052] L11 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,

[0053] Ar11 is any one of the following formulae B-1 to B-10,

[0054] n is an integer from 0 to 4, and when n is 2 or more, the plurality of L11 are identical to or different from each other,

[0055] [Formula B-1]

[0056]

[0057] In formula B-1,

[0058] Any one of G2 to G4, S12 and S13 is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0059] [Formula B-2]

[0060]

[0061] In formula B-2,

[0062] X1 is N or CRa, X2 is N or CRb, and X3 is N or CRc,

[0063] At least two of X1 to X3 are N,

[0064] Any one of G2 to G4 and Ra to Rc is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0065] [Formula B-3]

[0066]

[0067] In formula B-3,

[0068] Any one of G5 to G8 is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0069] [Formula B-4]

[0070]

[0071] In formula B-4,

[0072] Any one of G9 to G15 is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0073] [Formula B-5]

[0074]

[0075] In formula B-5,

[0076] Any one of G16 to G21 is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0077] [Formula B-6]

[0078]

[0079] In formula B-6,

[0080] Any one of G22 to G27 is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0081] [Formula B-7]

[0082]

[0083] In formula B-7,

[0084] X4 is N or CRd, X5 is N or CRe, X6 is N or CRf, and X7 is N or CRg,

[0085] At least one of X4 to X7 is N,

[0086] Any one of G28 to G33 and Rd to Rg is a moiety bonded to L11 of formula B, and the others are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0087] [Formula B-8]

[0088]

[0089] In formula B-8,

[0090] Y2 is O, S, NQ4 or CQ5Q6,

[0091] Any one of G43 to G47 is a moiety bonded to L11 of formula B, and the rest and Q4 to Q6 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

[0092] [Formula B-9]

[0093]

[0094] In formula B-9,

[0095] Y3 is O, S or NQ7,

[0096] X8 is N or CRh, and X9 is N or CRi,

[0097] Any one of G48, G49, Rh and Ri is a moiety bonded to L11 of formula B, and the others and Q7 are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imido, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0098] [Formula B-10]

[0099]

[0100] In formula B-10,

[0101] Any one of G50 to G56 is a moiety bonded to L11 of formula B, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0102] In an exemplary embodiment of the present specification, in Formula B, L11 is a direct bond, or an arylene group having 6 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

[0103] According to another exemplary embodiment, in Formula B, L11 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dimethylfluorenylene group, or a substituted or unsubstituted naphthylene group.

[0104] According to still another exemplary embodiment, in Formula B, L11 is a direct bond, a phenylene group, a biphenylene group, a dimethylfluorenylene group, or a naphthylene group.

[0105] According to an exemplary embodiment of the present specification, in Formula B-1, any one of G2 to G4, S12 and S13 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0106] According to another exemplary embodiment of the present specification, in Formula B-1, any one of G2 to G4, S12 and S13 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen, phenyl, or pyridyl.

[0107] According to an exemplary embodiment of the present specification, in Formula B-2, any one of G2 to G4 and Ra to Rc is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0108] According to another exemplary embodiment of the present specification, in Formula B-2, any one of G2 to G4 and Ra to Rc is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen; an aryl group which is unsubstituted or substituted with a cyano group, an aryl group, a heterocyclic group substituted with an alkyl group, or an aryl group which is unsubstituted or substituted with an aryl group; or a heteroaryl group.

[0109] According to another exemplary embodiment of the present specification, in formula B-2, any one of G2 to G4 and Ra to Rc is a portion bonded to L11 of formula B, and the rest are the same or different from each other and are each independently hydrogen; a phenyl group that is unsubstituted or substituted with an aryl group, a heterocyclic group substituted with an alkyl group, or a heterocyclic group that is unsubstituted or substituted with an aryl group; a biphenyl group that is unsubstituted or substituted with a cyano group or a heterocyclic group; a terphenyl group; a naphthyl group that is unsubstituted or substituted with an aryl group or a heteroaryl group; a fluorenyl group that is unsubstituted or substituted with an alkyl group; a triphenylene group; a phenanthrenyl group; a phenanthene group; a pyridyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0110] According to another exemplary embodiment of the present specification, in Formula B-2, any one of G2 to G4 and Ra to Rc is a portion bonded to L11 of Formula B, and the others are the same or different from each other and are each independently hydrogen; unsubstituted or substituted with phenyl, terphenyl, carbazolyl, quinolyl, phenoxyl, substituted with phenyl, or substituted with methyl; biphenyl which is unsubstituted or substituted with cyano or carbazolyl; terphenyl; naphthyl which is unsubstituted or substituted with phenyl, pyridyl or dibenzofuranyl; fluorenyl which is unsubstituted or substituted with methyl; triphenylene; phenanthrenyl; phenanthrenyl; phenanthene; pyridyl; dibenzofuranyl; or dibenzothienyl.

[0111] According to an exemplary embodiment of the present specification, in Formula B-3, any one of G5 to G8 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a substituted or unsubstituted aryl group.

[0112] According to another exemplary embodiment of the present specification, in Formula B-3, any one of G5 to G8 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or an aryl group.

[0113] According to another exemplary embodiment of the present specification, in Formula B-3, any one of G5 to G8 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen, phenyl, or naphthyl.

[0114] According to an exemplary embodiment of the present specification, in Formula B-4, any one of G9 to G15 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a substituted or unsubstituted aryl group.

[0115] According to another exemplary embodiment of the present specification, in Formula B-4, any one of G9 to G15 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or an aryl group.

[0116] According to another exemplary embodiment of the present specification, in Formula B-4, any one of G9 to G15 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a phenyl group.

[0117] According to an exemplary embodiment of the present specification, in Formula B-5, any one of G16 to G21 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a substituted or unsubstituted aryl group.

[0118] According to another exemplary embodiment of the present specification, in Formula B-5, any one of G16 to G21 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or an aryl group.

[0119] According to another exemplary embodiment of the present specification, in Formula B-5, any one of G16 to G21 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen, phenyl, biphenyl, or naphthyl.

[0120] According to an exemplary embodiment of the present specification, in Formula B-6, any one of G22 to G27 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or an aryl group.

[0121] According to another exemplary embodiment of the present specification, in Formula B-6, any one of G22 to G27 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a phenyl group.

[0122] According to an exemplary embodiment of the present specification, in Formula B-7, any one of G28 to G33 and Rd to Rg is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen.

[0123] According to another exemplary embodiment of the present specification, Formula B-7 is represented by any one of the following structures.

[0124]

[0125] In the structure, definitions of G28 to G33 and Rd to Rg are the same as those in Formula B-7.

[0126] According to an exemplary embodiment of the present specification, in Formula B-8, any one of G43 to G47 is a portion bonded to L11 of Formula B, and the remainder and Q4 to Q6 are the same or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0127] According to another exemplary embodiment of the present specification, in Formula B-8, any one of G43 to G47 is a portion bonded to L11 of Formula B, and the remainder and Q4 to Q6 are the same as or different from each other and are each independently hydrogen, alkyl, or aryl.

[0128] According to another exemplary embodiment of the present specification, in Formula B-8, any one of G43 to G47 is a portion bonded to L11 of Formula B, and the remainder and Q4 to Q6 are the same or different from each other and are each independently hydrogen, methyl, or phenyl.

[0129] According to still another exemplary embodiment of the present specification, in Formula B-8, when Y2 is NQ4, G43 and Q4 are bonded to each other to form a substituted or unsubstituted ring.

[0130] According to still another exemplary embodiment of the present specification, in Formula B-8, when Y2 is NQ4, G43 and Q4 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

[0131] According to another exemplary embodiment of the present specification, in Formula B-8, when Y2 is NQ4, G43 and Q4 are bonded to each other to form a benzisoquinoline ring.

[0132] According to still another exemplary embodiment of the present specification, Formula B-8 is represented by any one of the following structures.

[0133]

[0134] In the structure, any one of G43 to G47, G144 to G147 and G244 to G247 is a portion bonded to L11 of formula B, and the rest and Q4 to Q6 are the same or different from each other and are each independently hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio ...alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkylthio, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted The present invention may be a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boronyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[0135] According to an exemplary embodiment of the present specification, in formula B-9, any one of G48, G49, Rh and Ri is a portion bonded to L11 of formula B, and the rest and Q7 are the same or different from each other and are each independently hydrogen, or a substituted or unsubstituted aryl group.

[0136] According to another exemplary embodiment of the present specification, in Formula B-9, any one of G48, G49, Rh and Ri is a portion bonded to L11 of Formula B, and the rest and Q7 are the same or different from each other and are each independently hydrogen, or an aryl group which is unsubstituted or substituted with a cyano group.

[0137] According to another exemplary embodiment of the present specification, in formula B-9, any one of G48, G49, Rh and Ri is a portion bonded to L11 of formula B, and the rest and Q7 are the same or different from each other and are each independently hydrogen, or an unsubstituted or cyano-substituted phenyl group.

[0138] According to still another exemplary embodiment of the present specification, Formula B-9 is represented by any one of the following structures.

[0139]

[0140] In the structure, definitions of G48, G49, Rh, Ri and Q7 are the same as those in Formula B-9.

[0141] According to still another exemplary embodiment of the present specification, Formula B-9 is represented by any one of the following structures.

[0142]

[0143] In the structure, definitions of G48, G49, Rh, Ri and Q7 are the same as those in Formula B-9.

[0144] According to an exemplary embodiment of the present specification, in Formula B-10, any one of G50 to G56 is a portion bonded to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or an aryl group.

[0145] According to another exemplary embodiment of the present specification, in Formula B-10, any one of G50 to G56 is a portion bonding to L11 of Formula B, and the rest are the same as or different from each other and are each independently hydrogen or a phenyl group.

[0146] In the substituted or unsubstituted amine group, the amine group can be an aryl amine group, a heteroaryl amine group, or an arylheteroaryl amine group, and the compound composed of sp3 carbon as the center and containing the substituted or unsubstituted amine group between the anode and the light-emitting layer has excellent characteristics of injection and transport of holes in carriers, because the aryl and / or heteroaryl group bonded to the amine group has an electron donor tendency in aromatic compounds and heteroaromatic compounds due to the hyperconjugated structural effect about the sp3 carbon atom to enrich the distribution of electrons in the compound and make the p-type tendency strong.

[0147] According to an exemplary embodiment of the present invention, the “substituted or unsubstituted amine group” is represented by Formula A below.

[0148] [Formula A]

[0149]

[0150] In formula A,

[0151] L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

[0152] Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or are bonded to each other to form a substituted or unsubstituted heterocyclic ring,

[0153] p, r and q are each an integer from 0 to 4, and when p, r and q are each 2 or more, the substituents in the brackets are the same as or different from each other, and

[0154] *Indicates the position to be bonded.

[0155] In an exemplary embodiment of the present invention, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heteroaryl group having 2 to 30 carbon atoms.

[0156] According to an exemplary embodiment of the present invention, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolylene group, or a substituted or unsubstituted pyridylene group.

[0157] According to an exemplary embodiment of the present invention, L1 is a direct bond, or an arylene group having 6 to 30 carbon atoms.

[0158] In an exemplary embodiment of the present invention, L1 is a direct bond, or a phenylene group.

[0159] According to an exemplary embodiment of the present invention, L2 and L3 are the same as or different from each other and are each independently a direct bond, or an arylene group having 6 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms.

[0160] According to another exemplary embodiment, L2 and L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent 9,9-dimethylfluorenyl group, a divalent 9,9-diphenylfluorenyl group, a divalent spirofluorenyl group, a divalent phenanthryl group, or a divalent triphenylene group.

[0161] In an exemplary embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

[0162] In another exemplary embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen; an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted triarylsilyl group having 18 to 30 carbon atoms; an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a trimethylsilyl group, or an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms; or are bonded to each other to form a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0163] According to another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen; triphenylmethyl; phenyl which is unsubstituted or substituted with methyl, propyl, butyl, or trimethylsilyl; biphenyl; terphenyl; quaterphenyl; 9,9-dimethylfluorenyl; 9,9-diphenylfluorenyl; methylphenylfluorenyl; spirofluorenyl; naphthyl; dibenzofuranyl; naphthiobenzofuranyl; dibenzothienyl; N-phenylcarbazolyl; carbazolyl; triphenylsilyl; phenanthrenyl; triphenylene; or phenylspiruacridinefluorene; Or bond with each other to form a carbazole group; Oxazine Dimethylacridinyl Phenylphenazine Phenothiazine

[0164] According to an exemplary embodiment of the present invention, one or more layers in the second organic material layer contain one or more compounds each centered on an sp3 carbon, each of which contains a substituted or unsubstituted nitrogen-containing aromatic 5-membered ring, a substituted or unsubstituted nitrogen-containing aromatic 6-membered ring, or a substituted or unsubstituted nitrogen-containing aromatic polycyclic ring.

[0165] In addition, the nitrogen-containing aromatic 5-membered ring, the nitrogen-containing aromatic 6-membered ring and the substituted or unsubstituted nitrogen-containing aromatic polycyclic ring contained in the second organic material layer can improve the performance of the device because the amine compound composed of sp3 carbon at the center can be positioned in the first organic material layer to control the speed and injection of carriers, so that a balance of carriers can be formed and suitable for organic materials exhibiting excellent hole characteristics, and due to the structural characteristics, the durability of holes that can be applied to the light-emitting layer is excellent.

[0166] In an exemplary embodiment of the present invention, a first organic material layer including one or more compounds each centered on sp3 carbon and a second organic material layer including one or more compounds each centered on sp3 carbon are provided in contact with the light emitting layer. In this case, there is an advantage that by improving the carrier characteristics of the organic light emitting device, the performance of the device is improved and its service life is increased.

[0167] According to an exemplary embodiment of the present invention, the compound composed of sp3 carbon as the center may be represented by the following Formula 1, but is not limited thereto.

[0168] [Formula 1]

[0169]

[0170] In formula 1,

[0171] C is sp3 carbon, and

[0172] A1 to A4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[0173] Examples of the substituent in the present invention will be described below, but are not limited thereto.

[0174] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substitution position is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0175] In the present invention, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a silyl group, a boron group, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an amino group, an aryl group, or a heterocyclic group, substituted with a substituent in which two or more of the exemplified substituents are linked, or there is no substituent.

[0176] In the present invention, heterocyclic and heteroaryl groups contain O, S or N as heteroatoms.

[0177] According to an exemplary embodiment of the present invention, A1 to A4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 3 to 60 carbon atoms.

[0178] In another exemplary embodiment of the present invention, A1 to A4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 3 to 40 carbon atoms.

[0179] According to another exemplary embodiment, A1 to A4 are the same as or different from each other, and are each independently a substituted or unsubstituted methyl, a substituted or unsubstituted ethyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted The present invention relates to a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, or a substituted or unsubstituted quinazolinyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 3 to 40 carbon atoms.

[0180] In an exemplary embodiment of the present invention, adjacent groups among A1 to A4 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 40 carbon atoms; or a substituted or unsubstituted heterocycle having 3 to 40 carbon atoms containing O, S or N as a heteroatom.

[0181] According to an exemplary embodiment of the present invention, Formula 1 is represented by any one of Formulas 2 to 7 below.

[0182] [Formula 2]

[0183]

[0184] [Formula 3]

[0185]

[0186] [Formula 4]

[0187]

[0188] [Formula 5]

[0189]

[0190] [Formula 6]

[0191]

[0192] [Formula 7]

[0193]

[0194] In equations 2 to 7,

[0195] R101 to R104 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or are bonded to each other to form an aliphatic hydrocarbon ring,

[0196] R1 to R24 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkylsulfonyl group; a substituted or unsubstituted arylsulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

[0197] m1, m2, and m5 to m20 are each an integer from 0 to 4,

[0198] m3, m4, and m21 to m24 are each an integer from 0 to 5, and

[0199] When m1 to m24 are each 2 or more, two or more substituents in brackets are the same as or different from each other.

[0200] According to an exemplary embodiment of the present invention, R1 to R24 are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 40 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 6 to 60 carbon atoms, The present invention may be a substituted or unsubstituted arylsulfonyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 8 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclyl group having 2 to 60 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[0201] In an exemplary embodiment of the present invention, R101 to R104 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are bonded to each other to form an aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

[0202] According to another exemplary embodiment, R101 to R104 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group, or are bonded to each other to form a substituted or unsubstituted pentene ring.

[0203] In yet another exemplary embodiment, R101 to R104 are the same as or different from each other, and are each independently hydrogen, a methyl group, an ethyl group, or a phenyl group, or are bonded to each other to form a pentene ring.

[0204] According to an exemplary embodiment of the present invention, m1 to m24 are each an integer of 0 to 2, and when m1 to m24 are each 2, two substituents in brackets are the same as or different from each other.

[0205] According to an exemplary embodiment of the present invention, Formula 1 is represented by any one of Formulae 8 to 13 below.

[0206] [Formula 8]

[0207]

[0208] [Formula 9]

[0209]

[0210] [Formula 10]

[0211]

[0212] [Formula 11]

[0213]

[0214] [Formula 12]

[0215]

[0216] [Formula 13]

[0217]

[0218] In equations 8 to 13,

[0219] R105 to R108 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,

[0220] R25 to R50 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

[0221] m25 to m32, m34 to m39, and m41 to m50 are each an integer from 0 to 4,

[0222] m33 is an integer from 0 to 5,

[0223] m40 is an integer from 0 to 3, and

[0224] When m25 to m50 are each an integer of 2 or more, two or more substituents in the brackets are the same as or different from each other.

[0225] In an exemplary embodiment of the present invention, R105 to R108 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0226] According to another exemplary embodiment, R105 to R108 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

[0227] In yet another exemplary embodiment, R105 to R108 are the same as or different from each other, and are each independently hydrogen, methyl, or phenyl.

[0228] According to an exemplary embodiment of the present invention, R1 to R50 are hydrogen, deuterium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl having 6 to 60 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, formula A, or formula B, or are bonded to each other to form a substituted or unsubstituted aromatic ring having 2 to 30 carbon atoms.

[0229] In another exemplary embodiment, R1 to R50 are hydrogen, deuterium, cyano, triphenylsilyl, methyl, butyl, methoxy, phenyl which is unsubstituted or substituted with cyano or diphenylphosphine oxide, naphthyl which is unsubstituted or substituted with cyano, biphenyl which is unsubstituted or substituted with cyano, terphenyl which is unsubstituted or substituted with cyano or methoxy substituted with a halogen group, diphenylphosphine oxide, Formula A, or Formula B, or are bonded to each other to form substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzofuran, or substituted or unsubstituted naphthofuran.

[0230] According to an exemplary embodiment of the present invention, m25 to m50 are each an integer of 0 to 2, and when m25 to m50 are each 2, two substituents in brackets are the same as or different from each other.

[0231] In an exemplary embodiment of the present invention, the compound composed of sp3 carbon as the center may be any one of the following structures of [Group A] and [Group B], and according to an exemplary embodiment of the present invention, one or more layers in the organic material layer arranged between the anode and the light-emitting layer may include any one of the following structures of [Group A], and one or more layers in the organic material layer arranged between the cathode and the light-emitting layer may include any one of the following structures of [Group B].

[0232] [Group A]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348] [Group B]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538] According to an exemplary embodiment of the present invention, the light emitting layer may include a compound composed of sp3 carbon as a center.

[0539] In another exemplary embodiment, the light emitting layer may not include a compound composed of sp3 carbon as a center.

[0540] According to yet another exemplary embodiment, the light emitting layer includes a dopant, and the dopant may include one or more selected from the group consisting of the compound represented by Formula 1 above, a compound represented by Formula 101 below, and a compound represented by Formula 102 below, but is not limited thereto.

[0541] [Formula 101]

[0542]

[0543] In formula 101,

[0544] A, B and C are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle, and A and B may be connected through O, N—R401, S, Si or Se,

[0545] Y1 is B,

[0546] W1 and W2 are the same or different from each other and are each independently O, N—R402, S or Se,

[0547] R401 and R402 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are bonded to one or more substituents among A, B, and C to form a substituted or unsubstituted ring,

[0548] [Formula 102]

[0549]

[0550] In formula 102,

[0551] R301 to R310 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group.

[0552] According to an exemplary embodiment of the present specification, Formula 101 is represented by the following Formula 101-1.

[0553] [Formula 101-1]

[0554]

[0555] In formula 101-1,

[0556] Definitions of Y1, W1 and W2 are the same as those defined in Formula 101, and

[0557] R201 to R211 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heterocyclic group, or bond with an adjacent group to form a substituted or unsubstituted ring.

[0558] According to an exemplary embodiment of the present specification, when a compound composed of sp3 carbon as the center is included as a dopant of the light-emitting layer, the dopant may be any one selected from the following group C, but is not limited thereto. By introducing the compound composed of sp3 carbon as the center into the light-emitting layer, the injection and transport of carriers can be adjusted in the compound of the light-emitting layer to cause high color purity and efficiency.

[0559] [Group C]

[0560]

[0561]

[0562]

[0563] According to an exemplary embodiment of the present specification, when the light emitting layer includes a dopant, and the dopant is not a compound composed of sp3 carbon as the center, the dopant may be any one selected from the following Group D, but is not limited thereto.

[0564] [Group D]

[0565]

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573] In an exemplary embodiment of the present invention, the host of the light emitting layer includes one or more anthracene-based compounds.

[0574] According to an exemplary embodiment of the present invention, a host of the light emitting layer includes one or more anthracene-based compounds, and the anthracene-based compounds may be represented by the following Formula 2-1 or 2-2.

[0575] [Formula 2-1]

[0576]

[0577] [Formula 2-2]

[0578]

[0579] In formulas 2-1 and 2-2,

[0580] L201 to L205 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0581] Ar201 to Ar205 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,

[0582] R51 and R52 are the same as or different from each other and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0583] m51 is an integer of 0 to 8, and when m51 is 2 or more, the plurality of R51 are the same as or different from each other, and

[0584] m52 is an integer of 0 to 7, and when m52 is 2 or greater, the plurality of R52 are the same as or different from each other.

[0585] According to an exemplary embodiment of the present specification, L201 to L205 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0586] According to another exemplary embodiment, L201 to L205 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted terphenylene group.

[0587] In an exemplary embodiment of the present specification, Ar201 to Ar205 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0588] According to another exemplary embodiment, Ar201 to Ar205 are the same as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms which is unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

[0589] According to yet another exemplary embodiment, Ar201 to Ar205 are the same as or different from each other and are each independently a phenyl group which is unsubstituted or substituted with deuterium, a cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a biphenyl group which is unsubstituted or substituted with deuterium, a cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a atom; terphenyl, which is unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; fluorenyl, which is unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; spirofluorenyl, which is unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; thienyl substituted with a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; indolocarbazolyl, which is unsubstituted or substituted with a deuterium, a cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; dibenzofuranyl, which is unsubstituted or substituted with a deuterium, a cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; dibenzothiophene group substituted with an alkyl group having 6 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms; spirofluorenylxanthenyl group unsubstituted or substituted with deuterium, cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; spirofluorenylthioxanthenyl group unsubstituted or substituted with deuterium, cyano group, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or unsubstituted or substituted with deuterium, cyano, a trialkylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms

[0590] In an exemplary embodiment of the present invention, the case where the compound represented by formula 2-1 or 2-2 is not a compound centered on sp3 carbon is exemplified in the following group E, and the case where the compound represented by formula 2-1 or 2-2 is a compound centered on sp3 carbon is exemplified in the following group F, but the case is not limited thereto.

[0591] [Group E]

[0592]

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602] [Group F]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609] According to an exemplary embodiment of the present invention, the host of the light emitting layer includes two or more compounds.

[0610] In an exemplary embodiment of the present invention, the light emitting layer includes a fluorescent dopant, and the fluorescent dopant includes a non-pyrene-based compound.

[0611] According to an exemplary embodiment of the present invention, the non-pyrene-based compound is a compound constructed with sp3 carbon as the center, and the compound constructed with sp3 carbon as the center includes two or more substituted or unsubstituted amine groups.

[0612] In an exemplary embodiment of the present invention, the non-pyrene-based compound is a boron-based compound.

[0613] In an exemplary embodiment of the present invention, the organic light emitting device has a maximum emission peak at a wavelength of 400 nm to 470 nm.

[0614] According to another exemplary embodiment, an organic light emitting device has a maximum emission peak at a wavelength of 400 nm to 470 nm, and includes a non-pyrene-based compound as a dopant of a light emitting layer.

[0615] The emission spectrum of an organic light-emitting device requires high color purity according to the purpose, and the efficiency based thereon significantly affects the overall performance of the device. The color purity of the emission spectrum may vary depending on the dopant structure of the light-emitting layer and the correlation between the host and the dopant, and the case of including a boron-based compound as a non-pyrene-based compound as a dopant for the light-emitting layer has an advantage that the efficiency is improved by the service life of the device or high color purity, compared with the case of including a pyrene-based compound as a dopant for the light-emitting layer.

[0616] When one component of the present invention is disposed “on” another component, this includes not only a case where one component is in contact with another component but also a case where another component exists between the two components.

[0617] When a part of the present invention “comprises” a constituent element, unless otherwise specifically stated, this does not mean that other constituent elements are excluded but means that other constituent elements may also be included.

[0618] According to an exemplary embodiment of the present specification, a compound composed of sp3 carbon as a center may be included in a hole transport layer, a hole blocking layer, and an electron transport layer of an organic light emitting device.

[0619] In another exemplary embodiment, the compound composed of sp3 carbon as the center may be included in a hole transport layer, a hole blocking layer, an electron transport layer, and an electron blocking layer of an organic light emitting device.

[0620] According to yet another exemplary embodiment, a compound composed of sp3 carbon as a center may be included in a hole transport layer, an electron blocking layer, and a hole blocking layer of an organic light emitting device.

[0621] The organic light emitting device may have a stack structure such as described below, but the stack structure is not limited thereto.

[0622] (1) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0623] (2) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0624] (3) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0625] (4) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0626] (5) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0627] (6) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0628] (7) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0629] (8) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0630] (9) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0631] (10) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0632] (11) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0633] (12) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0634] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0635] The structure of the organic light emitting device of the present invention may have Figure 1 The structure shown in, but not limited to this.

[0636] Figure 1 The structure of an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8 and a cathode 9 are sequentially stacked on a substrate 1 is illustrated.

[0637] Figure 2 The structure of an organic light-emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 10, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8 and a cathode 9 are sequentially stacked on a substrate 1 is illustrated.

[0638] The organic light-emitting device according to the present invention can be manufactured by the following process: by using a physical vapor deposition (PVD) method (such as sputtering or electron beam evaporation) to deposit a metal or a conductive metal oxide, or an alloy thereof on a substrate to form an anode, an organic material layer having one or more layers selected from the following is formed on the anode: a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a layer for simultaneously transporting and injecting holes, a hole blocking layer, a layer for simultaneously transporting and injecting electrons, an electron transport layer, and an electron injection layer, and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above method, the organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0639] In addition, when manufacturing an organic light-emitting device according to the present invention, the compound can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0640] The organic material layer may also have a multilayer structure including a hole injection layer, a hole transport layer, a hole blocking layer, a layer for simultaneously injecting and transporting holes, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, etc., but is not limited thereto, and may have a single-layer structure.

[0641] The anode is an electrode for injecting holes, and as an anode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0642] The cathode is an electrode that injects electrons, and as a cathode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto. In addition, the cathode may be formed as one or two layers.

[0643] The materials for the organic material layer for the organic light emitting device exemplified below exemplify materials that may be included when each layer does not include the above-mentioned compound composed of central sp3 carbon, and are not limited thereto.

[0644] The hole injection layer is a layer for promoting the injection of holes from the anode into the light-emitting layer, and the hole injection material is preferably a material that can well accept holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on The hole injection layer may be an organic material, anthraquinone, a polyaniline-based conductive polymer, a polythiophene-based conductive polymer, etc., but is not limited thereto. The thickness of the hole injection layer may be 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage that the hole injection characteristic can be prevented from being deteriorated, and when the thickness of the hole injection layer is 150 nm or less, there is an advantage that the driving voltage can be prevented from being increased due to the hole injection layer being too thick in order to improve the movement of holes.

[0645] The hole transport layer can be used to smoothly transport holes. The hole transport material is suitably a material with high hole mobility, which can accept holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0646] In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and for the electron blocking layer, a material known in the art may be used.

[0647] The light-emitting layer can emit blue light, and the material used for the light-emitting layer is a material that can accept holes and electrons from the hole transport layer and the electron transport layer respectively and combine the holes and electrons to emit light in the visible light region, and corresponds to a material with high quantum efficiency for fluorescence or phosphorescence.

[0648] The electron transport layer can be used to smoothly transport electrons. The electron transport material is suitably a material with high electron mobility, which can well accept electrons from the cathode and transfer the electrons to the light-emitting layer. The thickness of the electron transport layer can be 1nm to 50nm. When the thickness of the electron transport layer is 1nm or more, it has the advantage of preventing the electron transport characteristics from deteriorating, and when the thickness of the electron transport layer is 50nm or less, it has the advantage of preventing the drive voltage from increasing due to the electron transport layer being too thick to improve the movement of electrons.

[0649] The electron injection layer can be used to smoothly inject electrons. The electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the cathode, and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated from the light-emitting layer from moving to the hole injection layer, and has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, Tetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0650] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0651] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can be disposed between the electron transport layer and the light emitting layer, and can generally be formed under the same conditions as the hole injection layer. Specific examples of hole blocking materials include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0652] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-side emission type according to the materials used.

[0653] Embodiments of the invention

[0654] Hereinafter, the present specification will be described in detail with reference to the embodiments that specifically describe the present specification. However, the embodiments according to the present specification can be modified in various forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully illustrate the present specification to those of ordinary skill in the art.

[0655] The compounds used in the following experimental examples are as follows.

[0656]

[0657]

[0658] Among the compounds, PD1 is synthesized by using the synthesis method described in Korean Patent No. 10-1188391 B1 or partially modifying the synthesis method, HT1 is synthesized by using the synthesis method described in Japanese Patent No. 5133259 B2 or partially modifying the synthesis method, HT2 is synthesized by using the synthesis method described in U.S. Patent No. 9917258 B2 or partially modifying the synthesis method, HT3 is synthesized by using the synthesis method described in Korean Patent No. 10-0645028 B1 or partially modifying the synthesis method, HT4 is synthesized by using the synthesis method described in Chinese Patent Application No. 2015-10845527 or partially modifying the synthesis method, and HT5 is synthesized by using the synthesis method described in Korean Patent Application Laid-Open No. 10-2014-0135117A or partially modifying the synthesis method. The invention relates to a method for synthesizing EB1 by using the synthesis method described in Japanese Patent No. 5608095B2 or partially modifying the synthesis method, EB2 by using the synthesis method described in Korean Patent No. 10-1605987B1 or partially modifying the synthesis method, EB3 by using the synthesis method described in Korean Patent Application Laid-Open No. 10-2015-0036654A or partially modifying the synthesis method, EB4 by using the synthesis method described in Korean Patent No. 10-0671862B1 or No. 10-0645052B1 or partially modifying the synthesis method, EB5 by using the synthesis method described in European Patent No. The synthesis method described in Korean Patent Application No. 3080229B1 or partially modified the synthesis method, BH1 is synthesized by using the synthesis method described in Korean Patent Application Laid-Open No. 10-2016-0089693A or partially modified the synthesis method, BD1 is synthesized by using the synthesis method described in Japanese Patent No. 5202730B2 or partially modified the synthesis method, BD2 is synthesized by using the synthesis method described in Korean Patent Application Laid-Open No. 10-2018-0004032A or partially modified the synthesis method, HB1 is synthesized by using the synthesis method described in U.S. Patent No. 6821643B1 or partially modifying the synthesis method, HB2 is synthesized by using the synthesis method described in Korean Patent No. 10-1755986B1 or partially modifying the synthesis method, HB3 is synthesized by using the synthesis method described in Korean Patent No. 10-1737199A or partially modifying the synthesis method, HB4 is synthesized by using the synthesis method described in Korean Patent No. 10-1737199B1 or 10-1542714B1 or partially modifying the synthesis method, HB5 is synthesized by using the synthesis method described in Korean Patent Application No. 10-2018-0042396 or partially modifying the synthesis method,ET1 was synthesized by using the synthesis method described in Japanese Patent No. 5194596 or partially modifying the synthesis method, ET2 and ET3 were synthesized by using the synthesis method described in Korean Patent No. 10-1832084B1 or partially modifying the synthesis method, ET4 was synthesized by using the synthesis method described in Korean Patent No. 10-1542714B1 or partially modifying the synthesis method, and ET5 was synthesized by using the synthesis method described in Korean Patent No. 10-1593368B1 or partially modifying the synthesis method. ,

[0659] <Experimental example>

[0660] Example 1. Fabrication of OLED

[0661] As the anode, ITO / Ag / ITO were deposited on it. The substrate with a thickness of 50 mm × 50 mm × 0.5 mm was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. A product manufactured by Fischer Co. was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic waves were repeatedly washed twice for 10 minutes using distilled water. After the washing with distilled water was completed, ultrasonic waves were washed using isopropyl alcohol, acetone and methanol solvents in this order, and then dried.

[0662] HT2 was thermally vacuum deposited onto the anode thus prepared. The thickness of the film was 0.5 and PD1 (2 wt%) was co-deposited to form a hole injection layer, and HT2 as a hole transporting material was vacuum deposited on the hole injection layer. Then, the host BH1 and the dopant BD1 (2 wt %) were vacuum deposited onto the Thereafter, HB2 is deposited to The thickness of the hole blocking layer is formed, and ET2 and Liq are mixed in a ratio of 5:5 to form a Subsequently, magnesium and lithium fluoride (LiF) are deposited on The thickness of the electron injection layer is formed <eil>A film of magnesium and silver (1:4) is used to form a thickness of The cathode is then deposited with CP1 In the above steps, the deposition rate of the organic materials is kept at / Second.

[0663] The configurations of the devices in Examples 2 to 28 and Comparative Examples 1 to 23 and the materials forming each layer are shown in Table 2 below, and the organic light emitting devices of Examples 2 to 28 and Comparative Examples 1 to 23 were manufactured by the same method as in Example 1.

[0664] Compounds each composed of sp3 carbon as a center used in each of the hole transport region, the electron transport region and the light emitting layer proposed by the experimental example of the present invention (applied to the embodiment, a total of three or more compounds) are as follows.

[0665] *Hole transport region

[0666] -Hole transport layer: HT2 to HT5

[0667] -Hole regulation layer: EB2 to EB5

[0668] *Electron transport zone

[0669] -Electronic regulation layer: HB2 to HB5

[0670] -Electron transport layer: ET2 to ET5

[0671] The compound not composed of sp3 carbon as the center used in each of the hole transport region, the electron transport region and the light emitting layer proposed by the experimental example of the present invention (applied to the comparative example) is as follows.

[0672] *Hole transport region

[0673] -Hole transport layer: HT1

[0674] -Hole regulation layer: EB1

[0675] *Electron transport zone

[0676] -Electronic regulation layer: HB1

[0677] -Electron transport layer: ET1

[0678] The band gap energy (E bg ).

[0679] [Table 1]

[0680]

[0681] The results of implementing one or more types (three or more compounds for all light-emitting devices) of the proposed compounds each centered on sp3 carbon in the hole transport region, electron transport region and light-emitting layer are shown in Examples 1 to 28, and comparisons of organic light-emitting devices composed of configurations that do not satisfy the aforementioned conditions are shown in Comparative Examples 1 to 23, and therefore various configurations and results of the devices are shown in Tables 2 and 3.

[0682] In Table 3 below, at 20 mA / cm 2 The voltage (V) and luminous efficiency (Cd / A) were measured at a current density of 20 mA / cm 2 The time taken for the luminance to become 95% of the initial luminance was measured at a current density of . In addition, the application number in Table 3 below means the number of compounds each composed of sp3 carbon as a center contained in the organic light-emitting device excluding the light-emitting layer.

[0683] [Table 2]

[0684]

[0685]

[0686]

[0687] [Table 3]

[0688]

[0689]

[0690]

[0691] According to the present invention, a total of three or more compounds each consisting of sp3 carbon as the center are necessarily applied to the first organic material layer (hole transport zone) and the second organic material layer (electron transport zone), and compared with the comparative example, the organic electroluminescent device manufactured by combining a total of three or more compounds shows excellent device performance. The compound consisting of sp3 carbon as the center is introduced into the hole transport zone and the electron transport zone to allow the device to have relatively fast carrier transport and delivery characteristics of holes and electrons, and allows the carriers injected from the positive electrode side and the negative electrode side to reach a balance in the light-emitting layer. In addition, by applying the compound consisting of sp3 carbon as the center to the light-emitting zone, the injection and movement of carriers in the light-emitting layer, energy transfer, etc. show effective light emission.

[0692] The hole transport region is composed of one or more hole transport layers and one or more electron blocking layers, the electron transport region is composed of one or more hole blocking layers and electron transport layers, and the results of the device according to the case in which the aforementioned compound composed of sp3 carbon as the center is introduced into each layer are determined.

[0693] Examples 1 to 5 are examples in which a total of three compounds each composed of sp3 carbon as the center are introduced into the first organic material layer (hole transport region) and the second organic material layer (electron transport region), but the electron blocking layer is not introduced into the first organic material layer. It can be observed that Examples 1 to 5 do not include an electron blocking layer and therefore show relatively low service life results compared to Examples 6 to 11 because the ability to regulate holes in the hole transport region is reduced, so that carrier balance is not formed, but Examples 1 to 5 cause excellent device performance compared to Comparative Example 1 in which a compound composed of sp3 carbon as the center is not introduced.

[0694] The results of Examples 1 to 11 show the results of applying three compounds each centered on sp3 carbon. It can be observed that, unlike Examples 1 to 11, Examples 12 to 28 can maximize the performance of an organic light-emitting device manufactured by introducing compounds each centered on sp3 carbon as a compound used in the first organic material layer (hole transport region) and the second organic material layer (electron transport region). Since the movement of carriers to the main body allows carriers to be transported and injected proportionally on both sides of the anode and cathode, low voltage and high efficiency are exhibited by maximizing the formation of excitons in the light-emitting layer. Therefore, the excellent durability of the hole blocking layer and the electron blocking layer used as a barrier is also maintained, thereby showing advantages in terms of service life.

[0695] In contrast, in Comparative Example 1 in which a compound composed of sp3 carbon as the center is not used, a balance of carriers is formed, but the results of high voltage, low efficiency and service life can be observed due to the limitation of device performance caused by the smooth supply. Compared with Examples 1 to 28, Comparative Examples 2 to 16 show the results caused by the imbalance of carriers because a compound composed of sp3 carbon as the center is used in one layer of the hole transport region and the electron transport region. Comparative Examples 17 to 23 show better performance of organic electroluminescent devices than Comparative Examples 2 to 16 due to the balance of carriers because a compound composed of sp3 carbon as the center is used in each of the hole transport region and the electron transport region, but show differences from the case of Examples 1 to 28 in which a total of three or more compounds each composed of sp3 carbon as the center are used.

[0696] Therefore, it can be determined that in Examples 1 to 28 and Comparative Examples 1 to 23, a total of three or more compounds, each of which is centered on sp3 carbon, can be used in the hole transport region and the electron transport region of the blue organic light-emitting device of the present invention to maximize the improvement in the injection and transport of carriers in the hole transport region and the electron transport region.< / eil>

Claims

1. An organic light-emitting device, comprising: anode; a cathode disposed facing the anode; A light-emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the anode and the light-emitting layer; and a second organic material layer disposed between the cathode and the light-emitting layer; Among the organic materials contained in the light-emitting layer, the first organic material layer and the second organic material layer, the band gap energy E of each organic material except the dopant compound is bg is 3eV or more, The first organic material layer comprises one or more compounds each of which is composed of sp3 carbon as the center, The second organic material layer comprises one or more compounds each of which is composed of sp3 carbon as a center, and The first organic material layer and the second organic material layer contain three or more compounds each having sp3 carbon as a center, The compound composed of the sp3 carbon as the center is represented by any one of the following formulae 2 to 13: [Formula 2] [Formula 3] [Formula 4] [Formula 5] [Formula 6] [Formula 7] In equations 2 to 7, R101 to R104 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are bonded to each other to form an aliphatic hydrocarbon ring, R1 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, m1, m2, and m5 to m20 are each an integer from 0 to 4, m3, m4, and m21 to m24 are each an integer from 0 to 5, and When m1 to m24 are each 2 or greater, two or more substituents in brackets are the same as or different from each other; [Formula 8] [Formula 9] [Formula 10] [Formula 11] [Formula 12] [Formula 13] In equations 8 to 13, R105 to R108 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, R25 to R33, and R36 to R50 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring, R34 and R35 are the same as or different from each other and are each independently hydrogen or deuterium, m25 to m32, m34 to m39, and m41 to m50 are each an integer from 0 to 4, m33 is an integer from 0 to 5, m40 is an integer from 0 to 3, and When m25 to m50 are each an integer of 2 or more, two or more substituents in the brackets are the same as or different from each other. 2 . The organic light-emitting device according to claim 1 , wherein the first organic material layer and the second organic material layer contain three to six compounds each having an sp 3 carbon as a center.

3. The organic light-emitting device according to claim 1, wherein one or more layers in the first organic material layer comprises one or more compounds each of which is composed of an sp3 carbon as the center, wherein the compound composed of an sp3 carbon as the center comprises a substituted or unsubstituted amine group, and One or more layers in the second organic material layer contain one or more compounds each centered on an sp3 carbon, wherein the sp3 carbon-centered compound contains a substituted or unsubstituted nitrogen-containing aromatic 5-membered ring, a substituted or unsubstituted nitrogen-containing aromatic 6-membered ring, or a substituted or unsubstituted nitrogen-containing aromatic polycyclic ring.

4. An organic light-emitting device according to claim 1, wherein the first organic material layer containing one or more compounds each centered on sp3 carbon and the second organic material layer containing one or more compounds each centered on sp3 carbon are arranged in contact with the light-emitting layer. The organic light emitting device according to claim 1 , wherein the organic light emitting device has a maximum emission peak at a wavelength of 400 nm to 470 nm. 6 . The organic light-emitting device according to claim 1 , wherein the light-emitting layer comprises a compound having sp 3 carbon as a center. 7 . The organic light emitting device according to claim 1 , wherein the light emitting layer comprises a host, and the host comprises two or more compounds. 8 . The organic light emitting device according to claim 1 , wherein the light emitting layer comprises a fluorescent dopant, and the fluorescent dopant comprises a non-pyrene-based compound.

9. The organic light-emitting device according to claim 8, wherein the non-pyrene-based compound is a compound composed of an sp3 carbon as the center, and the compound composed of an sp3 carbon as the center contains two or more substituted or unsubstituted amine groups. 10 . The organic light emitting device according to claim 8 , wherein the non-pyrene-based compound is a boron-based compound. 11 . The organic light emitting device according to claim 1 , wherein the light emitting layer comprises a host, and the host comprises one or more anthracene-based compounds.

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