Compound and organic light emitting device comprising the same

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device containing the same.

Description

Technology Field

[0001] This specification relates to a compound and an organic light-emitting device containing the same. Background Technology

[0002] In this specification, an organic light-emitting device refers to a light-emitting device utilizing an organic semiconductor material, which requires the exchange of holes and / or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly classified into two types based on their operating principles as follows. The first is a light-emitting device in which excitons are formed in an organic layer by photons introduced into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are each transferred to different electrodes to be used as current sources (voltage sources). The second is a light-emitting device in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and the device operates based on the injected electrons and holes.

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron suppression layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, and high contrast.

[0004] Materials used as organic layers in organic light-emitting diodes can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials. Light-emitting materials are classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors.

[0005] In addition, a host / dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap and superior luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated from the host are transported to the dopant to emit high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0006] In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, so the development of new materials is continuously required. Prior art literature

[0007] International Patent Publication No. 2017-126443 The problem to be solved

[0008] The present specification describes a compound and an organic light-emitting device containing the same. means of solving the problem

[0009] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X1 is O or S, and

[0014] A is the chemical formula 2 below, and

[0015] [Chemical Formula 2]

[0016]

[0017] One of R1 to R9 is bonded to ** of Formula 3 below, and the remaining substituents not bonded to ** of Formula 3 are the same or different from one another and are each independently hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted silyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amine group, or substituted or unsubstituted heteroaryl group, and

[0018] [Chemical Formula 3]

[0019]

[0020] In the above chemical formula 3,

[0021] L1 and L2 are the same or different from each other, and each is independently a directly bonded, substituted, or unsubstituted arylene group, and

[0022] R10 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted silyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amine group, or substituted or unsubstituted heteroaryl group, and

[0023] Ar1 is an aryl group substituted or unsubstituted with one or more of deuterium, nitrile, cycloalkyl, alkyl, and aryl groups, and

[0024] z is an integer from 1 to 8, and when z is 2 or greater, R10 are equal to or different from each other, and

[0025] p is an integer from 1 to 4, and when p is 2 or greater, Ar1 is the same or different.

[0026] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the aforementioned compound. Effects of the invention

[0027] The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the light-emitting layer of an organic light-emitting device, an organic light-emitting device having a high color reproduction rate can be manufactured. Brief explanation of the drawing

[0028] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention. Specific details for implementing the invention

[0029] The present specification will be described in more detail below.

[0030] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0031] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0032] Examples of substituents in this specification are described below, but are not limited thereto.

[0033] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0034] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group (-CN); silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or substituted with a substituent in which two or more of the exemplified substituents are connected, or not having any substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0035] Examples of the above substituents are described below, but are not limited thereto.

[0036] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0037] In the present specification, the silyl group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, etc. Specifically, the silyl group includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0038] In the present specification, the boron group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the boron group may be a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, etc., but is not limited thereto.

[0039] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it 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 yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0040] In this specification, the amine group may be selected from the group consisting of -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., are included, but are not limited thereto.

[0041] In this specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.

[0042] In this specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group.

[0043] In this specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.

[0044] In this specification, the alkyl groups among the alkylamine groups, N-arylalkylamine groups, alkylthioxy groups, alkyl sulfoxy groups, and N-alkylheteroarylamine groups are the same as the examples of alkyl groups described above. Specifically, alkylthioxy groups include methylthioxy groups; ethylthioxy groups; tert-butylthioxy groups; hexylthioxy groups; octylthioxy groups, etc., and alkyl sulfoxy groups include methyl sulfoxy groups; ethyl sulfoxy groups; propyl sulfoxy groups; butyl sulfoxy groups, etc., but are not limited thereto.

[0045] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0046] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0047] In the present specification, the heteroaryl group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. Examples of heteroaryl groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, etc.

[0048] In this specification, the arylene group is as defined in the aryl group, except that it is a divalent group.

[0049] In this specification, the heteroarylene group is as defined in the heteroaryl group, except that it is a divalent group.

[0050] The present invention relates to an anthracene compound in which a benzofuroindole unit containing oxygen and nitrogen, or a benzothioindole unit containing sulfur and nitrogen, is introduced. The compound of the present invention is used as a blue fluorescent host, which can improve the characteristics of existing blue fluorescent hosts and improve the performance (voltage, efficiency, lifespan, etc.) of blue light-emitting devices.

[0051] In one embodiment of the present specification, the formula 1 is the following formula 1-1 or 1-2.

[0052] [Chemical Formula 1-1]

[0053]

[0054] [Chemical Formula 1-2]

[0055]

[0056] In the above chemical formulas 1-1 and 1-2, R1 to R9 are as defined in chemical formula 1.

[0057] In one embodiment of the present specification, the formula 1 is the following formula 1-3 or 1-4.

[0058] [Chemical Formula 1-3]

[0059]

[0060] [Chemical Formula 1-4]

[0061]

[0062] In the above chemical formulas 1-3 and 1-4, R1 to R9 are as defined in chemical formula 1.

[0063] In the present specification, X1 is O.

[0064] In the present specification, X1 is S.

[0065] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded, or substituted or unsubstituted, arylene groups having 6 to 30 carbon atoms.

[0066] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded, or substituted or unsubstituted, arylene groups having 6 to 20 carbon atoms.

[0067] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded, or substituted or unsubstituted arylene groups having 6 to 15 carbon atoms.

[0068] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded or are arylene groups having 6 to 30 carbon atoms.

[0069] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded or are arylene groups having 6 to 20 carbon atoms.

[0070] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded or are arylene groups having 6 to 15 carbon atoms.

[0071] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent naphthalene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent phenanthrene group, a substituted or unsubstituted divalent pyrene group, or a substituted or unsubstituted divalent triphenylene group.

[0072] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent naphthalene group, a divalent biphenyl group, a divalent terphenyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent pyrene group, or a divalent triphenylene group.

[0073] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent naphthalene group, a divalent biphenyl group, a divalent terphenyl group, or a divalent anthracene group.

[0074] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent naphthalene group, or a divalent biphenyl group.

[0075] In one embodiment of the present specification, R9 is bonded to ** of Formula 3, or is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted silyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amine group, or substituted or unsubstituted heteroaryl group.

[0076] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group.

[0077] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0078] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, a silyl group, a cycloalkyl group, an amine group, or a heteroaryl group.

[0079] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a silyl group, a cycloalkyl group having 3 to 30 carbon atoms, an amine group, or a heteroaryl group having 3 to 30 carbon atoms.

[0080] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, an alkyl group, an aryl group, a cycloalkyl group, or a heteroaryl group.

[0081] In one embodiment of the present specification, R9 is hydrogen, deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0082] In one embodiment of the present specification, R9 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

[0083] In one embodiment of the present specification, R9 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0084] In one embodiment of the present specification, R9 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 15 carbon atoms.

[0085] In one embodiment of the present specification, R9 is an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0086] In one embodiment of the present specification, R9 is a methyl group or a phenyl group.

[0087] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from one another and are each independently hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted silyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amine group, or substituted or unsubstituted heteroaryl group.

[0088] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0089] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0090] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0091] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0092] In one embodiment of the present specification, one of R1 to R8 is bonded to ** of Formula 3, and the remaining substituents that are not bonded to ** of Formula 3 are the same or different from each other and are each independently hydrogen or deuterium.

[0093] In one embodiment of the present specification, R1 to R8 are the same or different from each other and are hydrogen or deuterium.

[0094] In one embodiment of the present specification, R1 among R1 to R8 is combined with ** of Formula 3.

[0095] In one embodiment of the present specification, R2 among R1 to R8 is combined with ** of Formula 3.

[0096] In one embodiment of the present specification, R3 among R1 to R8 is combined with ** of Formula 3.

[0097] In one embodiment of the present specification, R4 among R1 to R8 is combined with ** of Formula 3.

[0098] In one embodiment of the present specification, R5 among R1 to R8 is combined with ** of Formula 3.

[0099] In one embodiment of the present specification, R6 among R1 to R8 is combined with ** of Formula 3.

[0100] In one embodiment of the present specification, R7 among R1 to R8 is combined with ** of Formula 3.

[0101] In one embodiment of the present specification, R8 among R1 to R8 is combined with ** of Formula 3.

[0102] In one embodiment of the present specification, R10 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0103] In one embodiment of the present specification, R10 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0104] In one embodiment of the present specification, R10 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0105] In one embodiment of the present specification, R10 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0106] In one embodiment of the present specification, R10 is hydrogen, deuterium, methyl group, ethyl group, propyl group, butyl group, terbutyl group, phenyl group, biphenyl group, naphthyl group, anthracene group, phenanthrene group, pyrene group, or triphenylene group.

[0107] In one embodiment of the present specification, R10 is hydrogen, deuterium, methyl group, ethyl group, phenyl group, biphenyl group, or naphthyl group.

[0108] In one embodiment of the present specification, R10 is hydrogen, a phenyl group, a biphenyl group, or a naphthyl group.

[0109] In one embodiment of the present specification, the Ar1 is deuterium, a nitrile group, a cycloalkyl group, It is an aryl group substituted or unsubstituted with one or more of alkyl groups and aryl groups.

[0110] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more of deuterium, nitrile group, cycloalkyl group, alkyl group and aryl group.

[0111] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more of deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 3 to 30 carbon atoms.

[0112] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more of deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 3 to 30 carbon atoms.

[0113] In one embodiment of the present specification, Ar1 comprises: a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; a naphthyl group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; and a terphenyl group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms. Anthracene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; phenanthrene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; triphenylene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; fluorene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; A chrysene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; a benzofluorene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms; a spirobifluorene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms;Or it is a pyrene group substituted or unsubstituted with deuterium, a nitrile group, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 3 to 30 carbon atoms.;

[0114] In one embodiment of the present specification, Ar1 comprises a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a biphenyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a naphthyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a terphenyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; Anthracene group substituted or unsubstituted with deuterium, nitrile, cyclopentyl, cyclohexyl, methyl, ethyl, terbutyl, phenyl, naphthyl, or biphenyl groups; phenanthrene group substituted or unsubstituted with deuterium, nitrile, cyclopentyl, cyclohexyl, methyl, ethyl, terbutyl, phenyl, naphthyl, or biphenyl groups; triphenylene group substituted or unsubstituted with deuterium, nitrile, cyclopentyl, cyclohexyl, methyl, ethyl, terbutyl, phenyl, naphthyl, or biphenyl groups; fluorene group substituted or unsubstituted with deuterium, nitrile, cyclopentyl, cyclohexyl, methyl, ethyl, terbutyl, phenyl, naphthyl, or biphenyl groups; A chrysene group substituted or unsubstituted with a deuterium, nitrile group, cyclopentyl group, cyclohexyl group, methyl group, ethyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group; a benzoflurene group substituted or unsubstituted with a deuterium, nitrile group, cyclopentyl group, cyclohexyl group, methyl group, ethyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group; a spirobifluorene group substituted or unsubstituted with a deuterium, nitrile group, cyclopentyl group, cyclohexyl group, methyl group, ethyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group;or is a pyrene group substituted or unsubstituted with a deuterium, nitrile group, cyclopentyl group, cyclohexyl group, methyl group, ethyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group.;

[0115] In one embodiment of the present specification, Ar1 comprises: a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a biphenyl group substituted or unsubstituted with deuterium, a nitrile group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a naphthyl group substituted or unsubstituted with deuterium, a methyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; a terphenyl group substituted or unsubstituted with deuterium, a methyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; an anthracene group substituted or unsubstituted with deuterium, a methyl group, a terbutyl group, a phenyl group, a naphthyl group, or a biphenyl group; A phenanthrene group substituted or unsubstituted with a deuterium, methyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group; a triphenylene group substituted or unsubstituted with a deuterium, methyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group; or a fluorene group substituted or unsubstituted with a deuterium, methyl group, terbutyl group, phenyl group, naphthyl group, or biphenyl group.

[0116] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] The substituents of the compound of Chemical Formula 1 above may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0129] In addition, by introducing various substituents into a core structure having the structure described above, compounds possessing the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents primarily 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 core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0130] In addition, the organic light-emitting device according to the present invention comprises a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the aforementioned compound.

[0131] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0132] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0133] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer 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 comprising, as an organic layer, a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, etc. 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.

[0134] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among an electron transport layer, an electron injection layer, and a layer that performs electron injection and electron transport simultaneously, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0135] 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 a compound represented by the chemical formula 1.

[0136] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs hole injection and hole transport simultaneously, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0137] 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 a compound represented by the chemical formula 1.

[0138] In the organic light-emitting device of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a dopant material.

[0139] In the organic light-emitting device of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a compound of Formula 1.

[0140] In the organic light-emitting device of the present invention, the light-emitting layer comprises a host material and a dopant material, and the host material comprises a compound of Formula 1.

[0141] In the organic light-emitting device of the present invention, the light-emitting layer comprises a compound of Formula 1 as a host material.

[0142] In the organic light-emitting device of the present invention, the light-emitting layer comprises a compound of Formula 1 as a host material and comprises two or more dopant materials.

[0143] In the organic light-emitting device of the present invention, the light-emitting layer comprises a compound of Formula 1 as a host material and an organic compound as a dopant material.

[0144] In the organic light-emitting device of the present invention, the light-emitting layer comprises a compound of Formula 1 as a host material and a pyrene-based organic compound as a dopant material.

[0145] In the organic light-emitting device of the present invention, the light-emitting layer is a blue light-emitting layer.

[0146] In the organic light-emitting device of the present invention, the light-emitting layer comprises a host material and a dopant material in a weight ratio of 1:99 to 99:1.

[0147] In the organic light-emitting device of the present invention, the light-emitting layer comprises a host material and a dopant material in a weight ratio of 10:90 to 99:1.

[0148] In the organic light-emitting device of the present invention, the light-emitting layer comprises a host material and a dopant material in a weight ratio of 50:50 to 99:1.

[0149] In the organic light-emitting device of the present invention, the light-emitting layer comprises a host material and a dopant material in a weight ratio of 25:1 to 99:1.

[0150] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0151] According to another embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0152] (1) Anode / hole transport layer / emissive layer / cathode

[0153] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0154] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0155] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0156] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0157] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0158] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0159] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0160] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0161] (10) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0162] (11) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0163] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0164] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0165] (14) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0166] (15) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0167] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0168] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0169] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole blocking layer / electron injection and transport layer / cathode

[0170] The structure of the organic light-emitting device of the present invention may have a structure such as that shown in FIGS. 1 and 2, but is not limited thereto.

[0171] FIG. 1 illustrates 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, a compound represented by the chemical formula 1 may be included in the organic layer (3).

[0172] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), a hole control layer (7), a light-emitting layer (8), an electron control layer (9), an electron transport layer (10), an electron injection layer (11), and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, a compound represented by the chemical formula 1 may be included in the light-emitting layer (8).

[0173] For example, an organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer comprising one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that performs electron transport and electron injection simultaneously, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0174] The above organic layer may have 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 have a single layer structure. In addition, the above organic layer may be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0175] The above-mentioned anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0176] The above-mentioned cathode is an electrode for injecting electrons, and as the cathode material, it is preferable to have a material with a low work function to facilitate electron injection, typically an organic 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 materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0177] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, there is an advantage of preventing the driving voltage from rising to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0178] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0179] [Chemical Formula HT-1]

[0180]

[0181] In the above chemical formula HT-1,

[0182] At least one of X'1 to X'6 is N, and the rest are CH, and

[0183] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0184] According to one embodiment of the present specification, X'1 to X'6 are N.

[0185] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0186] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0187]

[0188] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0189] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0190] [Chemical Formula HT-2]

[0191]

[0192] In the above chemical formula HT-2,

[0193] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0194] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0195] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0196] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0197] According to one embodiment of the present specification, the R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0198] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0199] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and each independently is a phenyl group or combines with adjacent groups to form an indene substituted with a methyl group.

[0200] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0201]

[0202] A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0203] A hole control layer may be provided between the hole transport layer and the light-emitting layer. The hole control layer may be an arylamine compound or a material known in the art.

[0204] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0205] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic 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, pyrimidine derivatives, etc., but are not limited thereto.

[0206] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0207] According to one embodiment of the present specification, the dopant comprises a compound represented by the following chemical formula D-1, but is not limited thereto.

[0208] [Chemical Formula D-1]

[0209]

[0210] In the above chemical formula D-1,

[0211] T1 to T6 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0212] t5 and t6 are integers from 1 to 4, respectively, and

[0213] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other, and

[0214] If the above t6 is 2 or more, the above 2 or more T6s are the same or different from each other.

[0215] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0216] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a nitrile group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0217] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; an isopropyl group; a phenyl group substituted with a methyl group; or a dibenzofuran group.

[0218] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0219]

[0220] A hole suppression layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0221] The electron transport layer described above can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility, is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from degrading, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the electron transport layer being too thick.

[0222] As the organic compound of the electron transport layer, compounds of the chemical formula E1 below may be used, but are not limited thereto.

[0223] [Chemical Formula EI]

[0224]

[0225] In the above chemical formula E1,

[0226] X101 to X13 are the same or different from each other, and each is independently CH or N, and

[0227] At least one of X101 to X103 is N, and

[0228] Y101 to Y103 are the same or different from one another, and each independently is hydrogen; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0229] L111 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and

[0230] z00 is an integer from 1 to 10, and

[0231] When z00 is 2 or more, L111 are the same or different and are connected in series.

[0232] The phrase "connected in series" above means being connected in a straight line side by side, such as -phenyl-naphthyl- or -naphthyl-triazine-phenyl-.

[0233] In one embodiment of the present specification, X101 to X103 are N.

[0234] In one embodiment of the present specification, Y101 to Y103 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0235] In one embodiment of the present specification, L111 is an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0236] In one embodiment of the present specification, the chemical formula EI is the following compound.

[0237]

[0238] According to one embodiment of the present specification, the electronic control layer comprises a compound represented by the following chemical formula EI-1, but is not limited thereto.

[0239] [Chemical Formula EI-1]

[0240]

[0241] In the above chemical formula HI-1,

[0242] R301 to R304 are the same or different from one another, and each independently is 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 combines with adjacent groups to form a substituted or unsubstituted ring, and

[0243] r301 to r304 are each integers from 1 to 4, and

[0244] If the above r301 is 2 or more, the above R301 are the same or different from each other, and

[0245] If the above r302 is 2 or more, the above R302 are the same or different from each other, and

[0246] If the above r303 is 2 or more, the above R303 are the same or different from each other, and

[0247] If the above r304 is 2 or more, the above R304 are the same or different from each other.

[0248] According to the temporal state of the present specification, R301 to R304 are the same or different from one another and are each independently hydrogen, a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0249] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0250]

[0251] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0252] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, but are not limited thereto.

[0253] The hole blocking layer described above is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0254] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0255] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0256] The method for preparing the compound of Chemical Formula 1 above and the preparation of an organic light-emitting device using them will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0257] In the following reaction scheme, various types of intermediates can be synthesized by appropriately selecting known starting materials regarding the types and number of substituents. The types and conditions of the reaction and reaction conditions known in the art may be utilized.

[0258] By appropriately combining the manufacturing formulas described in the embodiments of this specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in this specification can be produced.

[0259] Preparation Example 1. Synthesis of A1 to A6 (Synthesis of A1-1 to A1-4, A2-1 to A2-5, A3-1 to A3-4, A4-1 to A4-5, A5-1, and A6-1)

[0260]

[0261]

[0262] SM1 (1 eq) and SM2 (1.1 eq) were added to tetrahydrofuran (excess), followed by the addition of a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetracitriphenyl-phosphinopalladium (2 mol%). The mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers, and the mixture was columned with hexane and ethyl acetate to prepare the above chemical formulas A1 to A6.

[0263] Except for changing SM1 and SM2 in the synthesis method of the above chemical formulas A1 to A6, A1-1 to A1-4, A2-1 to A2-5, A3-1 to A3-4, A4-1 to A4-5, A5-1, and A6-1 of [Table A] were synthesized in the same way.

[0264] [Table A]

[0265]

[0266]

[0267]

[0268] Preparation Example 2. Synthesis of B1 to B6 (Synthesis of B1-1 to B1-4 and B2-1 to B2-5, B3-1 to B3-4, B4-1 to B4-5, B5-1, and B6-1)

[0269]

[0270]

[0271] SM1 (1 eq) and triphenylphosphine (3 eq) were dissolved in ortho-dichlorobenzene (excess) and heated under reflux and stirred for 3 hours. The temperature was lowered to room temperature to terminate the reaction, and the mixture was precipitated in hexane (excess). The filtrate was dissolved in toluene, extracted with water, and columned with hexane and ethyl acetate to prepare the above formulas B1 to B6.

[0272] Except for changing SM1 and SM2 in the synthesis method of the above chemical formulas B1 to B6, B1-1 to B1-4 and B2-1 to B2-5, B3-1 to B3-4, B4-1 to B4-5, B5-1, and B6-1 of [Table B] were synthesized in the same way.

[0273] [Table B]

[0274]

[0275]

[0276]

[0277] Preparation Example 3. C1 to C6 (Synthesis of C1-1 to C1-5, C2-1 to C2-6, C3-1 to C3-5, C4-1 to C4-9, C5-1, and C6-1)

[0278]

[0279]

[0280] SM1 (1eq), SM2 (2eq), and potassium phosphate (3eq) were added to xylene, followed by stirring and reflux. Then, [bis(tri-t-butylphosphine)]palladium (0.01eq) was added, and after confirming the end of the reaction after 5 hours, the mixture was cooled to room temperature. Ethanol and water were added, filtered, and the solid was dissolved in toluene, extracted with water, and columned with hexane and ethyl acetate to produce the above chemical formulas C1 to C6.

[0281] Except for changing SM1 and SM2 in the synthesis method of the above chemical formulas C1 to C6, C1-1 to C1-5, C2-1 to C2-6, C3-1 to C3-5, C4-1 to C4-9, C5-1, and C6-1 of [Table C] were synthesized in the same way.

[0282] [Table C]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] Preparation Example 4. D1 to D6 (Synthesis of D1-1 to D1-5, D2-1 to D2-6, D3-1 to D3-5, D4-1 to D4-9, D5-1, and D6-1)

[0289]

[0290]

[0291] SM1 (1 eq) and SM2 (1.3 eq) are added to 1,4-dioxane (12 times the mass ratio of SM1), potassium acetate (3 eq) is added, and the mixture is stirred and refluxed. Palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) are added after stirring in 1,4-dioxane for 5 minutes, and after confirming the end of the reaction after 2 hours, the mixture is cooled to room temperature. After adding ethanol and water, the mixture is filtered and purified by recrystallization with ethyl acetate and ethanol to prepare the above chemical formulas D1 to D6.

[0292] Except for changing SM1 and SM2 in the synthesis method of the above chemical formulas D1 to D6, D1-1 to D1-5, D2-1 to D2-6, D3-1 to D3-5, D4-1 to D4-9, D5-1, and D6-1 of [Table D] were synthesized in the same way.

[0293] [Table D]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] Preparation Example 5. Synthesis of E1 and E3 (Synthesis of E1-1 and E3-1)

[0300]

[0301] E1-1 and E3-1 of [Table E] were synthesized using the same method as the synthesis method of the above chemical formulas A1 to A4, except that SM1 and SM2 were changed.

[0302]

[0303]

[0304] Preparation Example 6. F1, F3 (Synthesis of F1-1, F3-1)

[0305]

[0306] F1-1 and F3-1 of [Table F] were synthesized using the same method as the synthesis method of the above chemical formulas D1 to D4, except that SM1 and SM2 were changed.

[0307] [Table F]

[0308]

[0309] Preparation Example 7 (Synthesis of Compounds 1 to 27)

[0310]

[0311]

[0312]

[0313]

[0314] After adding the above SM1 (1 eq) and SM2 (1.05 eq) to tetrahydrofuran (excess), a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF) was added, and tetracyclotriphenyl-phosphinopalladium (2 mol%) was added, followed by heating and stirring for 10 hours. The temperature was lowered to room temperature to terminate the reaction, and the aqueous potassium carbonate solution was removed to separate the layers. After confirming the termination of the reaction, the temperature was lowered to room temperature to remove the solvent, and the mixture was purified by recrystallization using toluene to prepare the following compounds 1 to 27.

[0315] Compounds 1 to 27 of the following [Table 1] were synthesized using the same method except that SM1 and SM2 were changed.

[0316] SM2 in [Table 1] below was prepared with the following scheme.

[0317] SM2 scheme

[0318]

[0319] SM2 Example 1>

[0320]

[0321] SM2 Example 2>

[0322]

[0323] SM2 of compounds 1 to 23 was prepared as a synthetic example as described above.

[0324] In addition, the Suzuki reaction is the same method as the synthesis of chemical formula A1, and bromination is the same method as the synthesis of chemical formula B1, except that SM1 and SM2 are changed.

[0325] [Table 1]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332] Preparation Example 7 (Synthesis of Compounds 28 to 31)

[0333]

[0334] Reactant (1 eq) and trifluoromethanesulfonic acid (cat.) were added to C6D6 (mass ratio of 10 to 50 times the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was finished, D2O (excess) was added and stirred for 30 minutes, after which trimethylamine (excess) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried with MgSO4, then heated with toluene to recrystallize, thereby obtaining compounds 28 to 31 of [Table 2] below.

[0335] Compounds 28 to 31 in [Table 2] below were synthesized using the same method except that SM1 and SM2 were changed.

[0336] The reactants in [Table 2] below were prepared by changing SM1 and SM2 in the same manner as in Preparation Example 7 above.

[0337] [Table 2]

[0338]

[0339]

[0340] [Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value.]

[0341] Deuterium substitution for the above product was referenced in the prior art of KR1538534.

[0342] <Example 1> Manufacturing of OLED

[0343] A substrate with 70 / 1000 / 70 Å ITO / Ag / ITO deposited as an anode was cut into 50 mm x 50 mm x 0.5 mm pieces, placed in distilled water containing a dispersant, and cleaned using ultrasound. A detergent from Fischer Co. was used, and distilled water that had been double-filtered through a Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water washing was completed, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvents, followed by drying.

[0344] A hole injection layer was formed by thermal vacuum deposition of HI-1 to a thickness of 50 Å on the prepared anode, and a hole transport layer was formed by vacuum deposition of HT1, a material that transports holes, to a thickness of 1150 Å on top of it. Next, a hole control layer was formed using EB1 (150 Å), and then a emitting layer was formed by vacuum deposition of host compound 1 synthesized in Preparation Examples 6 and 7 and dopant BD1 (2 wt%) to a thickness of 360 Å. After that, an electron control layer was formed by depositing ET1 to a thickness of 50 Å, and an electron transport layer with a thickness of 250 Å was formed by mixing compound ET2 and Liq in a weight ratio of 7:3. The device was completed by sequentially depositing a 50 Å thick film of magnesium and lithium fluoride (LiF) as an electron injection layer, forming a 200 Å film of magnesium and silver (1:4) as a cathode, and then depositing CP1 to a thickness of 600 Å. During the above process, the deposition rate of the organic material was maintained at 1 Å / sec.

[0345]

[0346] Examples 1 to 36 and Comparative Examples 1 to 6, which are experimental results of organic light-emitting devices prepared using compounds 1 to 31 synthesized in Preparation Examples 7 and 8 as host materials for the light-emitting layer and BD1 and BD2 as dopant materials for the light-emitting layer, are shown in [Table 3].

[0347] Experimental Example 20 mA / cm² Host dopant Voltage (V) (@20mA / cm²) 2 ) Cd / A(@20mA / cm 2 ) Color coordinates (x,y) Lifespan (T95, h) (@20mA / cm²) 2 ) Example 1 Compound 1 BD1 3.38 6.90 (0.135, 0.138) 68.5 Example 2 Compound 2 BD1 3.40 6.88 (0.134, 0.137) 65.1 Example 3 Compound 3 BD1 3.41 6.79 (0.134, 0.140) 66.0 Example 4 Compound 4 BD1 3.43 6.85 (0.134, 0.137) 65.1 Example 5 Compound 5 BD1 3.39 6.80 (0.134, 0.137) 67.1 Example 6 Compound 6 BD1 3.35 6.91 (0.135, 0.138) 63.8 Example 7 Compound 7 BD1 3.39 6.80 (0.134, 0.137) 66.2 Example 8 Compound 8 BD1 3.40 6.81 (0.134, 0.137) 65.0 Example 9 Compound 9 BD1 3.41 6.89 (0.135, 0.138) 66.8 Example 10 Compound 10 BD1 3.33 6.75 (0.134, 0.137) 64.2 Example 11 Compound 11 BD1 3.39 6.80 (0.134, 0.137) 67.8 Example 12 Compound 12 BD1 3.42 6.77 (0.134, 0.138) 69.0 Example 13 Compound 13 BD1 3.44 6.84 (0.134, 0.137) 70.1 Example 14 Compound 14 BD1 3.35 6.88 (0.135, 0.138) 66.5 Example 15 Compound 15 BD1 3.36 6.84 (0.135, 0.138) 64.2 Example 16 Compound 16 BD1 3.35 6.80 (0.134, 0.142) 67.9 Example 17 Compound 17 BD1 3.33 6.79 (0.135, 0.138) 65.8 Example 18 Compound 18 BD1 3.40 6.77 (0.135, 0.138) 68.0 Example 19 Compound 19 BD1 3.41 6.78 (0.134, 0.137) 66.0 Example 20 Compound 20 BD1 3.40 6.80 (0.135, 0.138) 67.2 Example 21 Compound 21 BD1 3.44 6.81 (0.134, 0.143) 64.5 Example 22 Compound 22 BD1 3.41 6.83 (0.135, 0.138) 69.4 Example 23 Compound 23 BD1 3.35 6.85 (0.134, 0.139) 66.3 Example 24 Compound 24 BD1 3.37 6.84 (0.134, 0.138) 63.0 Example 25 Compound 25 BD1 3.40 6.80 (0.134, 0.137) 66.8 Example 26 Compound 26 BD1 3.40 6.79 (0.134, 0.137) 69.0 Example 27 Compound 27 BD1 3.39 6.77 (0.134, 0.137) 66.7 Example 28 Compound 28 BD1 3.40 6.80 (0.134, 0.137) 75.8 Example 29 Compound 29 BD1 3.34 6.74 (0.134, 0.137) 73.5 Example 30 Compound 30 BD1 3.42 6.76 (0.134, 0.138) 76.8 Example 31 Compound 31 BD1 3.41 6.79 (0.135, 0.138) 72.8 Example 32 Compound 4 BD2 3.49 7.23 (0.131, 0.121) 59.1 Example 33 Compound 13 BD2 3.51 7.13 (0.131, 0.123) 61.4 Example 34 Compound 19 BD2 3.50 7.09 (0.131, 0.121) 57.4 Example 35 Compound 23 BD2 3.42 7.18 (0.132, 0.122) 54.8 Example 36 Compound 28 BD2 3.50 7.06 (0.131, 0.121) 63.8 Comparative Example 1 BH1 BD1 3.90 5.88 (0.134, 0.139) 40.8 Comparative Example 2 BH2 BD1 3.60 4.04 (0.134, 0.137) 18.3 Comparative Example 3 BH3 BD1 7.83 3.56 (0.134, 0.159) 4.1 Comparative Example 4 BH4 BD1 4.86 3.68 (0.134, 0.148) 8.5 Comparative Example 5 BH1 BD2 4.01 6.11 (0.122, 0.122) 35.0 Comparative Example 6 BH2 BD2 3.78 4.22 (0.132, 0.123) 10.5

[0348] The present invention aims to improve blue light-emitting devices by improving the characteristics of an anthracene blue fluorescent host that introduces benzofuroindole units containing oxygen and nitrogen. By presenting various derivatives known prior art in Comparative Examples 1 to 6, a significant improvement in the device performance of the blue device compared to the prior art can be observed.

[0349] Comparative Examples 2 and 6 are anthracene derivatives that are currently the most widely used in blue fluorescent hosts among the examples in the prior art, and although it is possible to induce a low voltage due to the influence of the dimethyl unit depending on the configuration of the device, they show very low characteristics in terms of efficiency and lifespan compared to the present invention.

[0350] In Comparative Examples 3 and 4, results were observed where the prior compounds were unsuitable for blue fluorescent devices because they had structures unsuitable for current fluorescent systems or blue devices, resulting in very high voltage, low efficiency, and a critically short lifetime.

[0351] An organic electroluminescent device composed of a compound derivative of the chemical formula according to the present invention can control the smooth injection of holes into the light-emitting layer by using the compounds of Preparation Examples 7 and 8 as a host for a blue organic electroluminescent device, and through the balance of holes and electrons of the organic light-emitting device according to the chemical structure, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability. Explanation of the symbols

[0352] 1: Substrate 2: Anode 3: Organic layer 4: Cathode 5: Hole injection layer 6: Precision Transport Layer 7: Hole control layer 8: Emissive layer 9: Electronic control layer 10: Electron transport layer 11: Electron injection layer

Claims

Claim 1 Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above Chemical Formula 1, X1 is O or S, and A is the following Chemical Formula 2, [Chemical Formula 2] R9 is bonded to ** of Chemical Formula 3 below, R1 to R8 are the same or different from each other, and each is independently hydrogen or deuterium, [Chemical Formula 3] In the above chemical formula 3, L1 and L2 are the same or different from each other and are each independently directly bonded; or are arylene groups substituted or unsubstituted with an alkyl group or an aryl group, R10 is hydrogen, deuterium, or an aryl group, Ar1 is an aryl group substituted or unsubstituted with one or more of deuterium, a nitrile group, a cycloalkyl group, an alkyl group, and an aryl group, z is an integer from 1 to 8, and when z is 2 or more, R10 are the same or different from each other, p is an integer from 1 to 4, and when p is 2 or more, Ar1 are the same or different from each other. Claim 2 The compound of 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 above chemical formulas 1-1 and 1-2, R1 to R9 are as defined in chemical formula 1. Claim 3 The compound of claim 1, wherein Chemical Formula 1 is the following Chemical Formula 1-3 or 1-4: [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-3 and 1-4, R1 to R9 are as defined in chemical formula 1. Claim 4 delete Claim 5 A compound according to claim 1, wherein L1 and L2 are the same or different from each other and are each independently directly bonded; or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms. Claim 6 delete Claim 7 A compound according to claim 1, wherein Ar1 is a carbon 6 to 30 aryl group substituted or unsubstituted with one or more of deuterium, a nitrile group, a carbon 3 to 10 cycloalkyl group, a carbon 1 to 10 alkyl group, and a carbon 6 to 30 aryl group. Claim 8 A compound according to claim 1, wherein R10 is hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms. Claim 9 A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: . Claim 10 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 3, 5, and 7 to 9. Claim 11 An organic light-emitting device according to claim 10, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound. Claim 12 An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises a host material and a dopant material, and the host material comprises the compound. Claim 13 An organic light-emitting device according to claim 11, wherein the light-emitting layer is a blue light-emitting layer. Claim 14 An organic light-emitting device according to claim 12, wherein the light-emitting layer comprises a host material and a dopant material in a weight ratio of 50:50 to 99:1.

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