Compound and organic light-emitting device comprising same

Abstract

The present specification discloses a compound of Chemical Formula 1 and an organic light emitting device comprising the same. Also disclosed is an organic light-emitting device comprising a first electrode, a second electrode provided so as to face the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, the one or more organic material layers containing the compound, at this time, the organic layer contains a compound represented by Chemical Formula 1, and in this case, the luminous efficiency, stability, lifespan, and the like of the device can be improved.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0035355 filed with the Korean Patent Office on March 17, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

[0003] In this specification, an organic light-emitting device is a light-emitting device that uses an organic semiconductor material and requires the exchange of holes and / or electrons between an electrode and the organic semiconductor material. Organic light-emitting devices can be roughly divided into the following two types according to their working principles. The first type is a light-emitting device that uses photons flowing into the device from an external light source to form excitons in an organic layer, and the excitons are separated into electrons and holes, which are respectively transferred to different electrodes and used as a current source (voltage source). The second type is a light-emitting device that applies a voltage or current to two or more electrodes, thereby injecting holes and / or electrons into the organic semiconductor material layer that forms an interface with the electrodes, and works through the injected electrons and holes.

[0004] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light emitting devices that utilize the phenomenon of organic light emitting generally have a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, and the like. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted. Such organic light emitting devices are known to have the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0005] Materials used as organic layers in organic light-emitting devices can be divided into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, electron injection materials, etc. According to the luminescent color, the light-emitting materials include blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials required to achieve better natural colors.

[0006] In addition, in order to increase the color purity and increase the luminous efficiency based on energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a dopant with a smaller energy band gap and excellent luminous efficiency than the host that mainly constitutes the luminescent layer is mixed in a small amount into the luminescent layer, the excitons generated in the host are transferred to the dopant and emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, light of the desired wavelength can be obtained according to the type of dopant used.

[0007] In order to give full play to the excellent characteristics of the above-mentioned organic light-emitting devices, the substances constituting the organic layer in the device, such as hole injection substances, hole transport substances, luminescent substances, electron suppression substances, electron transport substances, electron injection substances, etc., are backed by stable and effective materials, and therefore there is a continuous demand for the development of new materials. Summary of the invention

[0008] Technical issues

[0009] This specification describes a compound and an organic light-emitting device including the same.

[0010] Solution to the problem

[0011] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] X1 and X2 are the same as or different from each other and are each independently a triazine group, a pyrimidinyl group, a pyridinyl group, a quinazolinyl group or a quinolinyl group,

[0016] The above X1 and X2 are substituted by substituted or unsubstituted aryl groups,

[0017] L1 is a direct bond, an arylene group, or a substituted or unsubstituted heteroarylene group,

[0018] L2 is an arylene group, or a substituted or unsubstituted heteroarylene group,

[0019] Het is a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted benzo Azolyl,

[0020] a and b are each an integer from 1 to 3,

[0021] When a and b are 2 or more, the substituents in the brackets may be the same as or different from each other.

[0022] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, which includes: a first electrode, a second electrode arranged opposite to the above-mentioned first electrode, and one or more organic layers arranged between the above-mentioned first electrode and the above-mentioned second electrode, and one or more of the above-mentioned organic layers contain the above-mentioned compound.

[0023] Effects of the Invention

[0024] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured by including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage and long life characteristics can be obtained. When the compound of the present invention is included in the electron injection layer, electron transport layer, and electron injection and transport layer of the organic light-emitting device, due to the high intramolecular polarization, the electron transfer effect is good, and an organic light-emitting device having a long life characteristic can be manufactured.

[0025] The present invention relates to two N-containing monocyclic or bicyclic heterocyclic groups and benzimidazolyl, benzo A compound in which an azole or benzothiazolyl group is substituted on one benzene ring. In other words, three N-type substituents are substituted on one benzene ring. By having the above-mentioned form, electron migration is easy compared to substances with one or two N-type substituents, and thus high efficiency and low voltage effects can be expected. In addition, by adjusting the three N-type substituents, the electron mobility can be adjusted more accurately, and since the balance of the device can be coordinated, it is easy to find the optimal point of the efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 and 2 An example of an organic light emitting device according to the present invention is illustrated.

[0027] [Explanation of symbols]

[0028] 1: Substrate

[0029] 2: Anode

[0030] 3: Organic layer

[0031] 4: Cathode

[0032] 5: Hole injection layer

[0033] 6: First hole transport layer

[0034] 7: Second hole transport layer

[0035] 8: Luminous layer

[0036] 9: Electron injection and transport layer DETAILED DESCRIPTION

[0037] Next, this specification is described in more detail.

[0038] The benzimidazolyl, benzo The oxazolyl group and the benzothiazolyl group are substituted with one or more alkyl groups or aryl groups, and if the substitution is on the side of the five-membered ring, the stability of the substance can be ensured.

[0039] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0040] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0041] In the present specification, examples of substituents are described below, but are not limited thereto.

[0042] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0043] In this specification, the term "substituted or unsubstituted" means that the group is substituted by one or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, or is substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or has no substituent. For example, the "substituent formed by connecting two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups.

[0044] Examples of the above substituents are described below, but are not limited thereto.

[0045] In the present specification, as examples of the halogen group, there are fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0046] In the present specification, the silyl group may be substituted or unsubstituted by deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, etc. The above-mentioned silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0047] In the present specification, the boryl group may be substituted or unsubstituted by deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boryl group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.

[0048] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0049] In the present specification, the amine group can be selected from -NH2, alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroarylamine and heteroarylamine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methylanthrylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0050] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group.

[0051] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group.

[0052] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group.

[0053] In this specification, alkylamino, N-arylalkylamino, alkylthio Alkylsulfonyl The alkyl group in the N-alkylheteroarylamine group is the same as the alkyl group exemplified above. Specifically, as the alkylthio group, there are methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, etc., and as the alkylsulfonyl group, there are methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, etc., but it is not limited thereto.

[0054] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0055] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, yl, fluorenyl, etc., but are not limited to these.

[0056] In the present specification, the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. Examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0057] In the present specification, a ring refers to an aliphatic ring, an aromatic ring, a heterocyclic ring, or a condensed ring thereof. An aliphatic ring follows the definition of a cycloalkyl group except that it is not monovalent, an aromatic ring follows the definition of an aryl group except that it is not monovalent, and a heterocyclic ring follows the definition of a heteroaryl group except that it is not monovalent.

[0058] In one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-1 or 1-2.

[0059] [Chemical formula 1-1]

[0060]

[0061] [Chemical formula 1-2]

[0062]

[0063] In the above chemical formulas 1-1 and 1-2, X1, X2, L1, L2, a and b are the same as those in the above chemical formula 1.

[0064] Any one of R1 to R3 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group,

[0065] c is an integer from 1 to 3, and when c is 2 or more, the above R3 are the same or different from each other,

[0066] c' is an integer of 1 to 4, and when c' is 2 or more, the above R3 are the same as or different from each other.

[0067] In one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-3 or Chemical Formula 1-4.

[0068] [Chemical formula 1-3]

[0069]

[0070] [Chemical formula 1-4]

[0071]

[0072] In the above chemical formulas 1-3 and 1-4, X1, X2, L1, L2, a and b are the same as those in the above chemical formula 1.

[0073] One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group,

[0074] R6 is an alkyl group or an aryl group,

[0075] d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other,

[0076] e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

[0077] In one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-5 or 1-6.

[0078] [Chemical formula 1-5]

[0079]

[0080] [Chemical formula 1-6]

[0081]

[0082] In the above chemical formulas 1-5 and 1-6, X1, X2, L1, L2, a and b are the same as those in the above chemical formula 1.

[0083] One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group,

[0084] R6 is an alkyl group or an aryl group,

[0085] d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other,

[0086] e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

[0087] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1-1 to 1-1-6.

[0088] [Chemical formula 1-1-1]

[0089]

[0090] [Chemical formula 1-1-2]

[0091]

[0092] [Chemical formula 1-1-3]

[0093]

[0094] [Chemical formula 1-1-4]

[0095]

[0096] [Chemical formula 1-1-5]

[0097]

[0098] [Chemical formula 1-1-6]

[0099]

[0100] In the above chemical formulas 1-1-1 to 1-1-6, X1, X2, L1, L2, a and b are the same as those defined in the above chemical formula 1.

[0101] Any one of R1 to R3 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group,

[0102] c is an integer of 1 to 3, and when c is 2 or more, the above R3 are the same as or different from each other.

[0103] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1-7 to 1-1-16.

[0104] [Chemical formula 1-1-7]

[0105]

[0106] [Chemical formula 1-1-8]

[0107]

[0108] [Chemical formula 1-1-9]

[0109]

[0110] [Chemical formula 1-1-10]

[0111]

[0112] [Chemical formula 1-1-11]

[0113]

[0114] [Chemical formula 1-1-12]

[0115]

[0116] [Chemical formula 1-1-13]

[0117]

[0118] [Chemical formula 1-1-14]

[0119]

[0120] [Chemical formula 1-1-15]

[0121]

[0122] [Chemical formula 1-1-16]

[0123]

[0124] In the above chemical formulas 1-1-7 to 1-1-16, X1, X2, L1, L2, a and b are the same as those defined in the above chemical formula 1.

[0125] One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group,

[0126] R6 is an alkyl group or an aryl group,

[0127] d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other,

[0128] e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

[0129] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-10.

[0130] [Chemical formula 2-1]

[0131]

[0132] [Chemical formula 2-2]

[0133]

[0134] [Chemical formula 2-3]

[0135]

[0136] [Chemical formula 2-4]

[0137]

[0138] [Chemical formula 2-5]

[0139]

[0140] [Chemical formula 2-6]

[0141]

[0142] [Chemical formula 2-7]

[0143]

[0144] [Chemical formula 2-8]

[0145]

[0146] [Chemical formula 2-9]

[0147]

[0148] [Chemical formula 2-10]

[0149]

[0150] In the above Chemical Formulae 2-1 to 2-10, X1, X2, L1, L2, a, b and Het are the same as defined in the above Chemical Formula 1.

[0151] In one embodiment of the present specification, X1 and X2 are identical to each other.

[0152] In one embodiment of the present specification, X1 and X2 are different from each other.

[0153] In one embodiment of the present specification, X1 and X2 are triazine groups, which are substituted with substituted or unsubstituted aryl groups which are the same as or different from each other.

[0154] In one embodiment of the present specification, X1 and X2 are pyrimidinyl groups, which are substituted with substituted or unsubstituted aryl groups which are the same or different from each other.

[0155] In one embodiment of the present specification, X1 and X2 are pyridyl groups, which are substituted with substituted or unsubstituted aryl groups which are the same or different from each other.

[0156] In one embodiment of the present specification, X1 and X2 are quinolyl groups, which are substituted with substituted or unsubstituted aryl groups which are the same or different from each other.

[0157] In one embodiment of the present specification, X1 and X2 are quinazolinyl groups, which are substituted with substituted or unsubstituted aryl groups which are the same or different from each other.

[0158] In one embodiment of the present specification, the above X1 and X2 are substituted with an aryl group having 6 to 30 carbon atoms.

[0159] In one embodiment of the present specification, the above-mentioned X1 and X2 are substituted with an aryl group having 6 to 20 carbon atoms.

[0160] In one embodiment of the present specification, the above-mentioned X1 and X2 are substituted with an aryl group having 6 to 15 carbon atoms.

[0161] In one embodiment of the present specification, X1 and X2 are substituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group or a phenanthryl group.

[0162] In one embodiment of the present specification, X1 is a quinolyl group or a quinazolinyl group, and X2 is a triazine group, a pyrimidinyl group or a pyridinyl group.

[0163] In one embodiment of the present specification, X1 is a quinolyl group, and X2 is a triazine group, a pyrimidinyl group, or a pyridinyl group.

[0164] In one embodiment of the present specification, X1 is a quinazolinyl group, and X2 is a triazine group, a pyrimidinyl group, or a pyridinyl group.

[0165] In one embodiment of the present specification, X2 is a quinolyl group or a quinazolinyl group, and X1 is a triazine group, a pyrimidinyl group or a pyridinyl group.

[0166] In one embodiment of the present specification, X2 is a quinolyl group, and X1 is a triazine group, a pyrimidinyl group, or a pyridinyl group.

[0167] In one embodiment of the present specification, X2 is a quinazolinyl group, and X1 is a triazine group, a pyrimidinyl group, or a pyridinyl group.

[0168] In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently quinolyl or quinazolinyl, substituted with the same or different substituted or unsubstituted aryl.

[0169] In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are independently triazine, pyrimidinyl or pyridinyl, and are substituted with the same or different substituted or unsubstituted aryl groups.

[0170] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an arylene group having 6 to 30 carbon atoms.

[0171] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an arylene group having 6 to 20 carbon atoms.

[0172] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an arylene group having 6 to 15 carbon atoms.

[0173] In one embodiment of the present specification, L1 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracenyl group, or a divalent phenanthryl group.

[0174] In one embodiment of the present specification, L1 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent anthracenyl group, or a divalent phenanthryl group.

[0175] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

[0176] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an unsubstituted arylene group having 6 to 30 carbon atoms.

[0177] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an unsubstituted arylene group having 6 to 20 carbon atoms.

[0178] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or an unsubstituted arylene group having 6 to 15 carbon atoms.

[0179] In one embodiment of the present specification, L1 is a direct bond, an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, a divalent unsubstituted terphenyl group, a divalent unsubstituted naphthyl group, a divalent unsubstituted anthracenyl group, or a divalent unsubstituted phenanthryl group.

[0180] In one embodiment of the present specification, L1 is a direct bond, an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, a divalent unsubstituted naphthyl group, a divalent unsubstituted anthracenyl group, or a divalent unsubstituted phenanthryl group.

[0181] In one embodiment of the present specification, L1 is a direct bond, an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, or a divalent unsubstituted naphthyl group.

[0182] In one embodiment of the present specification, the above-mentioned L2 is an arylene group having 6 to 20 carbon atoms.

[0183] In one embodiment of the present specification, the above-mentioned L2 is an arylene group having 6 to 15 carbon atoms.

[0184] In one embodiment of the present specification, the above-mentioned L2 is a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracenyl group, or a divalent phenanthryl group.

[0185] In one embodiment of the present specification, the above-mentioned L2 is a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent anthracenyl group, or a divalent phenanthryl group.

[0186] In one embodiment of the present specification, the above-mentioned L2 is a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

[0187] In one embodiment of the present specification, the above-mentioned L2 is an unsubstituted arylene group having 6 to 20 carbon atoms.

[0188] In one embodiment of the present specification, the above-mentioned L2 is an unsubstituted arylene group having 6 to 15 carbon atoms.

[0189] In one embodiment of the present specification, L2 is an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, a divalent unsubstituted terphenyl group, a divalent unsubstituted naphthyl group, a divalent unsubstituted anthracenyl group, or a divalent unsubstituted phenanthryl group.

[0190] In one embodiment of the present specification, L2 is an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, a divalent unsubstituted naphthyl group, a divalent unsubstituted anthracenyl group, or a divalent unsubstituted phenanthryl group.

[0191] In one embodiment of the present specification, the above-mentioned L2 is an unsubstituted phenylene group, a divalent unsubstituted biphenyl group, or a divalent unsubstituted naphthyl group.

[0192] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] The substituents of the compound of the above Chemical Formula 1 can be combined by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0209] In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the above core structure, a material that meets the conditions required in each organic layer can be synthesized.

[0210] In addition, the organic light-emitting device according to the present invention is characterized in that it includes: a first electrode, a second electrode arranged opposite to the above-mentioned first electrode, and one or more organic layers arranged between the above-mentioned first electrode and the above-mentioned second electrode, and one or more of the above-mentioned organic layers contains the above-mentioned compound.

[0211] The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0212] The above compounds can be formed into an organic layer by not only vacuum evaporation method but also solution coating method when manufacturing organic light-emitting devices. Here, the so-called solution coating method refers to spin coating method, dip coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0213] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers or a larger number of organic layers.

[0214] In the organic light-emitting device of the present invention, the organic layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers may contain the compound represented by the above Chemical Formula 1.

[0215] In another organic light emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0216] In the organic light emitting device of the present invention, the electron injection and transport layer comprises the compound of the above Chemical Formula 1 and a metal complex.

[0217] In the organic light-emitting device of the present invention, the organic layer may include a hole injection layer, a hole transport layer, and one or more layers of a layer that simultaneously performs hole injection and hole transport, and one or more of the layers may contain the compound represented by the above Chemical Formula 1.

[0218] In another organic light emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1.

[0219] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0220] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0221] (1) Anode / hole transport layer / light-emitting layer / cathode

[0222] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0223] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0224] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0225] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0226] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0227] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0228] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0229] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0230] (10) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0231] (11) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0232] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0233] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0234] (14) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0235] (15) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0236] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0237] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0238] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0239] The structure of the organic light emitting device of the present invention may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.

[0240] Figure 1 exemplifies the structure of an organic light emitting device in which an anode 2, an organic layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound represented by the above chemical formula 1 may be contained in the above organic layer 3.

[0241] Figure 2 exemplifies the structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light-emitting layer 8, an electron injection and transport layer 9, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport layer 9.

[0242] For example, the organic light-emitting device according to the present invention can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then an organic layer including one or more layers selected from a hole injection layer, a hole transport layer, a layer for simultaneously performing hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously performing electron transport and electron injection is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0243] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and formed into a smaller number of layers by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0244] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); 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, but are not limited thereto.

[0245] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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, etc., but are not limited thereto.

[0246] The hole injection layer is a layer that plays a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick to improve the migration of holes.

[0247] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0248] [Chemical formula HI-1]

[0249]

[0250] In the above chemical formula HI-1,

[0251] R403 to R406 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0252] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0253] l403 is an integer from 1 to 3. When l403 is 2 or more, L403 are the same as or different from each other.

[0254] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are independently any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0255] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms substituted by an aryl group having 6 to 30 carbon atoms.

[0256] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, or a carbazolyl group substituted with a phenyl group.

[0257] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group or a carbazolyl group substituted with a phenyl group.

[0258] According to one embodiment of the present specification, L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0259] According to one embodiment of the present specification, the L403 is a phenylene group, a divalent dimethylfluorenyl group, or a divalent carbazolyl group which may be substituted with an aryl group.

[0260] According to one embodiment of the present specification, the above-mentioned L403 is a divalent dimethylfluorenyl group.

[0261] According to one embodiment of the present specification, the chemical formula HI-1 is the following compound.

[0262]

[0263] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.

[0264] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0265] [Chemical formula HT-1]

[0266]

[0267] In the above chemical formula HT-1,

[0268] At least one of X'1 to X'6 is N, and the others are CH,

[0269] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0270] According to one embodiment of the present specification, X'1 to X'6 are N.

[0271] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0272] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0273]

[0274] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HI-2, but is not limited thereto.

[0275] [Chemical formula HT-2]

[0276]

[0277] In the above chemical formula HT-2,

[0278] L311 to L313 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,

[0279] R311 to R313 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0280] According to one embodiment of the present specification, R311 to R313 are the same as or different from each other, and are each independently any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0281] According to one embodiment of the present specification, R311 to R313 are the same as or different from each other, and are independently any one selected from a substituted or unsubstituted carbazole group, a substituted or unsubstituted phenyl group, a biphenyl group, a dimethylfluorenyl group, and a combination thereof.

[0282] According to one embodiment of the present specification, L311 to L313 are the same as or different from each other, and are each independently a direct bond, an arylene group, or a heteroarylene group.

[0283] According to one embodiment of the present specification, L311 to L313 are the same as or different from each other, and are each independently a direct bond or a phenylene group.

[0284] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0285]

[0286] An electron suppression layer may be provided between the hole transport layer and the light emitting layer. The electron suppression layer may use the above-mentioned spiro compound or a material known in the technical field.

[0287] The above-mentioned light-emitting layer can emit red, green or blue light, and can be formed of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0288] The main material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0289] According to one embodiment of the present specification, the host includes a compound represented by the following chemical formula H-1, but is not limited thereto.

[0290] [Chemical formula H-1]

[0291]

[0292] In the above chemical formula H-1,

[0293] L20 and L21 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 divalent heterocyclic group,

[0294] Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0295] R201 is hydrogen, deuterium, a halogen group, 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,

[0296] r201 is an integer of 1 to 8. When r201 is 2 or more, two or more R201s are the same as or different from each other.

[0297] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0298] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0299] In one embodiment of the present specification, the Ar20 is a substituted or unsubstituted heterocyclic group, and the Ar21 is a substituted or unsubstituted aryl group.

[0300] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0301] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0302] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently substituted or unsubstituted phenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Thienyl substituted or unsubstituted by an aryl group having 6 to 20 carbon atoms; dibenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0303] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted by deuterium, a thienyl group substituted or unsubstituted by phenyl, a phenanthryl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group or a naphthiobenzothiophenyl group.

[0304] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other and are each independently a phenyl group.

[0305] According to one embodiment of the present specification, the above R201 is a phenyl group.

[0306] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0307]

[0308] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.

[0309] According to one embodiment of the present specification, the dopant is represented by a compound of the following chemical formula D-2.

[0310] [Chemical formula D-2]

[0311]

[0312] In the above chemical formula D-2,

[0313] T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted aryl group,

[0314] t3 and t4 are each an integer from 1 to 4,

[0315] t5 is an integer from 1 to 3,

[0316] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0317] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0318] When the above t5 is 2 or more, the above two or more T5s may be the same as or different from each other.

[0319] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0320] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0321] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are independently hydrogen, methyl, tert-butyl, biphenyl substituted with methyl, or phenyl substituted or unsubstituted with methyl or isopropyl.

[0322] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

[0323]

[0324] A hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0325] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1 to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0326] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0327] Examples of the metal coordination compounds include, but are not limited to, 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, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0328] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0329] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0330] The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0331] The method for producing the compound of the above Chemical Formula 1 and the production of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0332] In the following reaction formula, the type and number of substituents can be appropriately selected by a person skilled in the art from known starting materials to synthesize various types of intermediates. The type and conditions of the reaction can be based on techniques known in the art.

[0333] The method for producing the compound of the above Chemical Formula 1 and the production of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0334] In the following reaction formula, the type and number of substituents can be appropriately selected by a person skilled in the art from known starting materials to synthesize various types of intermediates. The type and conditions of the reaction can be based on techniques known in the art.

[0335] If the production formulae described in the examples of the present specification and the intermediates described above are appropriately combined based on common technical knowledge, all the compounds of the above Chemical Formula 1 described in the present specification can be produced.

[0336] Modes for Carrying Out the Invention

[0337] Manufacturing Example 1.

[0338]

[0339] Compound 1-1 (17.19 g, 60 mmol) and the above compound 1-2 (16.00 g, 60 mmol) were added to tetrahydrofuran (600 mL). 2M K2CO3 (400 mL) and tetrakis(triphenylphosphine)palladium(0) (0.6 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the generated solid was recrystallized twice from toluene to produce the above compound 1-3.

[0340] The above-mentioned compound 1-3 (14.22 g, 30 mmol) and the above-mentioned compound 1-4 (13.03 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL), palladium acetate (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and then stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered and the generated solid was recrystallized twice from toluene to produce the above-mentioned compound 1.

[0341] (16.33 g, yield 73%, MS: [M+H] + =746).

[0342] Manufacturing Example 2.

[0343]

[0344] The above-mentioned compound 2 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0345] MS:[M+H] + =734

[0346] Manufacturing Example 3.

[0347]

[0348] The above-mentioned compound 3 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0349] MS:[M+H] + =733

[0350] Manufacturing Example 4.

[0351]

[0352] The above-mentioned compound 4 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0353] MS:[M+H] + =736

[0354] Manufacturing Example 5.

[0355]

[0356] The above-mentioned compound 5 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0357] MS:[M+H] + =854

[0358] Manufacturing Example 6.

[0359]

[0360] The above-mentioned compound 6 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0361] MS:[M+H] + =809

[0362] Manufacturing Example 7.

[0363]

[0364] The above-mentioned compound 7 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0365] MS:[M+H] + =750

[0366] Manufacturing Example 8.

[0367]

[0368] The above-mentioned compound 8 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0369] MS:[M+H] + =864

[0370] Manufacturing Example 9.

[0371]

[0372] The above-mentioned compound 9 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0373] MS:[M+H] + =778

[0374] Production Example 10.

[0375]

[0376] The compound 10 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0377] MS:[M+H] + =781

[0378] Production Example 11.

[0379]

[0380] The above-mentioned compound 11 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0381] MS:[M+H] + =733

[0382] Production Example 12.

[0383]

[0384] The above-mentioned compound 12 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0385] MS:[M+H] + =707

[0386] Production Example 13.

[0387]

[0388] The above-mentioned compound 13 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0389] MS:[M+H] + =798

[0390] Production Example 14.

[0391]

[0392] The above-mentioned compound 14 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0393] MS:[M+H] + =810

[0394] Production Example 15.

[0395]

[0396] The above-mentioned compound 15 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0397] MS:[M+H] + =733

[0398] Production Example 16.

[0399]

[0400] The above-mentioned compound 16 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0401] MS:[M+H] + =810

[0402] Production Example 17.

[0403]

[0404] The above-mentioned compound 17 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0405] MS:[M+H] + =798

[0406] Production Example 18.

[0407]

[0408] The above-mentioned compound 18 was produced by the same method as the production method of the above-mentioned Production Example 1 except that each starting material was used as shown in the above-mentioned reaction formula.

[0409] MS:[M+H] + =782

[0410] [Example]

[0411] Example 1-1

[0412] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0413] On the ITO transparent electrode prepared in this way, the following compound HI-A was applied as A hole injection layer is formed by thermal vacuum deposition of a thickness of The following compounds HAT and The following compound HT-A was vacuum-deposited in sequence to form a first hole transport layer and a second hole transport layer.

[0414] Next, on the second hole transport layer, a film having a thickness of The following compound BH and compound BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

[0415] On the above-mentioned light-emitting layer, the compound 1 prepared above and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1, thereby On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0416]

[0417] In the above process, the evaporation rate of organic matter is maintained to Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 1*10 -7 Up to 5*10 -5 A support is provided to manufacture an organic light-emitting device.

[0418] Example 1-2 to Example 1-18

[0419] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that Compounds 2 to 18 described in Table 1 below were used instead of Compound 1 in Example 1-1.

[0420] Comparative Examples 1-1 to 1-6

[0421] Organic light-emitting devices were manufactured by the same method as in Example 1-1 except that compounds ET-1 to ET-7 in Table 1 were used instead of Compound 1 in Example 1-1. The structures of compounds ET-1 to ET-7 in Table 1 are shown below.

[0422]

[0423] [Experimental example]

[0424] For the organic light-emitting devices manufactured in the above Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-7, the 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) until the initial luminance reaches 90% was measured at a current density of . The results are shown in Table 1 below.

[0425] [Table 1]

[0426]

[0427] As shown in the above table 1, the compound represented by chemical formula 1 according to the present specification can be used in the organic layer responsible for electron transport of the organic light-emitting device. Comparative Examples 1-1, 1-2, 1-4, 1-6 and 1-7 use compounds in which neither X1 nor X2 is substituted or either one is substituted. In this case, compared with Examples 1-1 to 1-18 in which both X1 and X2 are substituted with aryl groups, the voltage is high, the efficiency is low, and the life is shortened.

[0428] Comparative Example 1-3 used the compound ET-3 in which Het is quinoxaline. Compared with Comparative Example 1-3, Examples 1-1 to 1-18 had higher voltage, lower efficiency, and shorter life.

[0429] In Comparative Example 1-5, L1 and L2 are directly bonded. In this case, compared with Examples 1-1 to 1-18 in which any one of L1 and L2 includes a linking group such as an arylene group or a heteroarylene group, the voltage is high, the efficiency is low, and the life is shortened.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X1 and X2 are the same as or different from each other and are each independently a triazine group, a pyrimidinyl group, a pyridinyl group, a quinazolinyl group or a quinolinyl group, The X1 and X2 are substituted by substituted or unsubstituted aryl groups, L1 is a direct bond, an arylene group, or a substituted or unsubstituted heteroarylene group, L2 is an arylene group, or a substituted or unsubstituted heteroarylene group, Het is a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiazolyl group, or a substituted or unsubstituted benzo Azolyl, a and b are each an integer from 1 to 3, When a and b are 2 or more, the substituents in the brackets may be the same as or different from each other.

2. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-1 or 1-2: [Chemical formula 1-1] [Chemical formula 1-2] In the chemical formulas 1-1 and 1-2, X1, X2, L1, L2, a and b are the same as those defined in the chemical formula 1. Any one of R1 to R3 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group, c is an integer from 1 to 3, and when c is 2 or more, the R3 are the same or different from each other, c' is an integer of 1 to 4. When c' is 2 or more, the R3's are the same or different from each other.

3. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-3 or 1-4: [Chemical formula 1-3] [Chemical formula 1-4] In the chemical formulas 1-3 and 1-4, X1, X2, L1, L2, a and b are the same as those in the chemical formula 1. One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group, R6 is an alkyl group or an aryl group, d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other, e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

4. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-5 or 1-6: [Chemical formula 1-5] [Chemical formula 1-6] In the chemical formulas 1-5 and 1-6, X1, X2, L1, L2, a and b are the same as those in the chemical formula 1. One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group, R6 is an alkyl group or an aryl group, d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other, e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

5. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1-1 to 1-1-6: [Chemical formula 1-1-1] [Chemical formula 1-1-2] [Chemical formula 1-1-3] [Chemical formula 1-1-4] [Chemical formula 1-1-5] [Chemical formula 1-1-6] In the chemical formulas 1-1-1 to 1-1-6, X1, X2, L1, L2, a and b are the same as those defined in the chemical formula 1. Any one of R1 to R3 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group, c is an integer of 1 to 3. When c is 2 or more, the R3 are the same or different from each other.

6. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1-7 to 1-1-16: [Chemical formula 1-1-7] [Chemical formula 1-1-8] [Chemical formula 1-1-9] [Chemical formula 1-1-10] [Chemical formula 1-1-11] [Chemical formula 1-1-12] [Chemical formula 1-1-13] [Chemical formula 1-1-14] [Chemical formula 1-1-15] [Chemical formula 1-1-16] In the chemical formulas 1-1-7 to 1-1-16, X1, X2, L1, L2, a and b are the same as those defined in the chemical formula 1. One of R4 and R5 is an alkyl group or an aryl group, and the others are hydrogen, deuterium, an alkyl group or an aryl group, R6 is an alkyl group or an aryl group, d is an integer from 1 to 3, and when d is 2 or more, R5 are the same or different from each other, e is an integer of 1 to 4, and when e is 2 or more, R6 are the same as or different from each other.

7. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 2-1 to 2-10: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6] [Chemical formula 2-7] [Chemical formula 2-8] [Chemical formula 2-9] [Chemical formula 2-10] In the Chemical Formulae 2-1 to 2-10, X1, X2, L1, L2, a, b and Het are the same as defined in the Chemical Formula 1.

8. The compound according to claim 1, wherein The X1 and X2 are identical to each other.

9. The compound according to claim 1, wherein The X1 and X2 are different from each other.

10. The compound according to claim 1, wherein The chemical formula 1 is any one of the following compounds:

11. An organic light emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 10.

12. The organic light emitting device according to claim 11, wherein: The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and at least one of the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

13. The organic light emitting device according to claim 11, wherein: The organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

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