Compounds and organic electronic devices comprising the same

Abstract

This specification provides for compounds of chemical formula 1 and organic electronic devices containing them.

Description

Technical Field

[0001] This specification relates to compounds and organic electronic devices containing them.

[0002] This application claims priority to Korean Patent Application No. 10-2021-0018331, filed with the Korean Patent Office on February 9, 2021, the contents of which are fully incorporated herein by reference. Background Technology

[0003] Organic light-emitting devices (OLEDs) are a representative example of organic electronic devices. Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. OLEDs typically have a structure including an anode and a cathode, and an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When this exciton re-enters the ground state, it emits light.

[0004] Most of the materials used in organic light-emitting devices (OLEDs) are pure organic substances or coordination compounds formed by organic substances and metals. These materials can be categorized according to their application as hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injection materials. Here, as hole injection or hole transport materials, organic substances with p-type properties are primarily used, i.e., organic compounds that are easily oxidized and electrochemically stable when oxidized. On the other hand, as electron injection or electron transport materials, organic substances with n-type properties are primarily used, i.e., organic compounds that are easily reduced and electrochemically stable when reduced. As the luminescent layer material, materials possessing both p-type and n-type properties are preferred, i.e., materials that are stable in both oxidized and reduced states, and materials with high luminescent efficiency when forming excitons are preferred.

[0005] In order to fully utilize the excellent characteristics of the aforementioned organic light-emitting devices, there is a continuous demand for the development of materials that constitute the organic layer within the device. Summary of the Invention

[0006] Technical issues

[0007] This specification relates to compounds and organic electronic devices containing them.

[0008] Solution to the problem

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

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] G1 and G2 may be the same as or different from each other, and each is independently hydrogen, deuterium, or represented by the following chemical formula 2, wherein at least one of G1 and G2 is represented by the following chemical formula 2.

[0014] a is an integer from 1 to 8. When a is 2 or higher, two or more G1 values ​​are either the same or different from each other.

[0015] b is an integer from 1 to 8. When b is 2 or higher, the two or more G2s are either the same or different from each other.

[0016] [Chemical Formula 2]

[0017]

[0018] In the above chemical formula 2,

[0019] R1 to R4 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0020] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0021] X is S, O, or CR5R6.

[0022] R5 and R6 may be the same as or different from each other, each being independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or adjacent groups may combine with each other to form a ring, two of Y1 to Y4 are N, and the rest are combined with L1 or L2.

[0023] The above m is an integer from 0 to 5.

[0024] The above n is an integer from 0 to 5.

[0025] The Z mentioned above represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0026] The asterisk (*) indicates the position where it combines with the above chemical formula 1.

[0027] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: 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 contain the aforementioned compound.

[0028] Invention Effects

[0029] The compounds described in this specification can be used as materials for the organic layers of organic electronic devices. When manufacturing organic electronic devices comprising the compounds according to at least one embodiment, organic electronic devices with low driving voltage and long lifespan can be obtained.

[0030] In particular, when the compounds of the present invention are used in the electron injection layer, electron blocking layer, electron transport layer and light-emitting layer, the driving voltage of the device can be reduced, and the device efficiency and lifetime can be increased. Attached Figure Description

[0031] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0032] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4.

[0033] [Symbol Explanation]

[0034] 1: Substrate

[0035] 2: Anode

[0036] 3: Emissive layer

[0037] 4: Cathode

[0038] 5: Hole injection layer

[0039] 6: Hole transport layer

[0040] 7: Emissive layer

[0041] 8: Layers that simultaneously perform electron injection and electron transport Detailed Implementation

[0042] The following is a more detailed description of this instruction manual.

[0043] This specification provides compounds of Formula 1 below. By combining compounds of Formula 1 below with compounds of Formula 2 below through substitution of at least one of the substituents in the nucleus, it is possible to achieve the effects of reduced device drive voltage, increased device efficiency, and extended device lifespan.

[0044] [Chemical Formula 1]

[0045]

[0046] In the above chemical formula 1,

[0047] G1 and G2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or represented by the following chemical formula 2.

[0048] At least one of G1 and G2 mentioned above is represented by the following chemical formula 2.

[0049] a is an integer from 1 to 8. When a is 2 or higher, two or more G1 values ​​are either the same or different from each other.

[0050] b is an integer from 1 to 8. When b is 2 or higher, the two or more G2s are either the same or different from each other.

[0051] [Chemical Formula 2]

[0052]

[0053] In the above chemical formula 2,

[0054] R1 to R4 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0055] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0056] X is S, O, or CR5R6.

[0057] R5 and R6 may be the same as or different from each other, each being independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or adjacent groups may combine with each other to form a ring, two of Y1 to Y4 are N, and the rest are combined with L1 or L2.

[0058] The above m is an integer from 0 to 5.

[0059] The above n is an integer from 0 to 5.

[0060] The Z mentioned above represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0061] The asterisk (*) indicates the position where it combines with the above chemical formula 1.

[0062] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0063] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0064] Throughout the description of this application, the term "combination thereof" in the Markush form refers to a mixture or combination of one or more constituent elements described in the Markush form, and means including one or more of the aforementioned constituent elements.

[0065] The substituents in this specification will be described in detail below, but are not limited thereto.

[0066] In this instruction manual, Indicates the site where it is bonded to other substituents or binding sites.

[0067] In this specification, the term "substitution" refers to the replacement of hydrogen atoms on carbon atoms of a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0068] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from deuterium (-D), halogen groups, cyano (-CN), nitro, alkyl, alkenyl, cycloalkyl, alkoxy, amino, silyl, aryl, and heteroaryl, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0069] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0070] In this specification, the alkyl group can be straight-chain, branched, or cyclic, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2 ...cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylbutyl, cyclobutyl, cyclopentyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylbutyl, cyclobutyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylbutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, 3-methylcyclopentyl, 2,3-dimethylbutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclo -Dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited to these.

[0071] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0072] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 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, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., are used, but are not limited to these.

[0073] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably ranges from 1 to 40. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0074] The alkyl, alkoxy, and other substituents containing alkyl moiety described in this specification include both straight-chain and branched forms.

[0075] In this specification, the amino group may be selected from -NH2, monoalkylamino, dialkylamino, N-alkylarylamino, monoarylamino, diarylamino, triarylamino, N-arylheteroarylamino, N-alkylheteroarylamino, monoheteroarylamino, and diheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, trimethylamino, ethylamino, diethylamino, triethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited to these.

[0076] In this specification, the silyl group can be composed of -SiY a Y b Y c The chemical formula of the above Y represents a Y b and Y cEach can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the aforementioned silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0077] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes methyl, fluorene, triphenylene, etc., but is not limited to these.

[0078] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0079] When the aforementioned fluorene group is replaced, it can be used as follows: (spirofluorene) (spirodifluorene) (9,9-dimethylfluorene) and The substituted fluorenyl groups include (9,9-diphenylfluorenyl) and others, but are not limited to these.

[0080] The aryl group can be replaced by an alkyl group to function as an alkylaryl group. The alkyl group can be selected from the examples above.

[0081] In this specification, a heteroaryl group is an aromatic cyclic group containing one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. The heteroaryl group can be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, pyrimidinyl, triazinyl, triazolyl, quinolinyl, quinazolinyl, carbazole, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, naphthobenzofuranyl, dibenzofuranyl, etc., but not limited to these.

[0082] In this specification, arylene refers to a group with two bonding sites on an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the same description of aryl groups as described above.

[0083] In this specification, a heteroaryl group refers to a group with two bonding sites on a heteroaryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heteroaryl groups.

[0084] In this specification, "adjacent" groups can refer to substituents that are directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted to the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0085] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0086] The aforementioned hydrocarbon ring can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. In addition to being a divalent group, it can be selected from the examples of cycloalkyl or aryl groups mentioned above.

[0087] In one embodiment of this specification, the above-mentioned chemical formula 2 can be any one of the following chemical formulas 2-1 to 2-12.

[0088] [Chemical Formula 2-1]

[0089]

[0090] [Chemical Formula 2-2]

[0091]

[0092] [Chemical Formula 2-3]

[0093]

[0094] [Chemical Formula 2-4]

[0095]

[0096] [Chemical Formula 2-5]

[0097]

[0098] [Chemical Formula 2-6]

[0099]

[0100] [Chemical Formula 2-7]

[0101]

[0102] [Chemical Formula 2-8]

[0103]

[0104] [Chemical Formula 2-9]

[0105]

[0106] [Chemical Formula 2-10]

[0107]

[0108] [Chemical Formula 2-11]

[0109]

[0110] [Chemical Formula 2-12]

[0111]

[0112] In the above chemical formulas 2-1 to 2-12,

[0113] X, R1 to R4, L1, L2, Z, m, n and * are defined in the same way as in the above chemical formula 2.

[0114] In one embodiment of this specification, G1 is represented by the above chemical formula 2, G2 is hydrogen or deuterium, and a is an integer from 1 to 8.

[0115] In one embodiment of this specification, G1 is represented by the above chemical formula 2, G2 is hydrogen or deuterium, and a is an integer from 1 to 4.

[0116] In one embodiment of this specification, G1 is represented by the above chemical formula 2, G2 is hydrogen or deuterium, and a is 1.

[0117] In one embodiment of this specification, G1 is hydrogen or deuterium, G2 is represented by the above chemical formula 2, and b is an integer from 1 to 8.

[0118] In one embodiment of this specification, G1 is hydrogen or deuterium, G2 is represented by the above chemical formula 2, and b is an integer from 1 to 4.

[0119] In one embodiment of this specification, G1 is hydrogen or deuterium, G2 is represented by the above chemical formula 2, and b is 1.

[0120] In one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 50 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms.

[0121] In one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms.

[0122] In one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0123] In one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each may be hydrogen or deuterium independently.

[0124] In one embodiment of this specification, each of R1 to R4 is hydrogen.

[0125] In one embodiment of this specification, each of R1 to R4 is deuterium.

[0126] In one embodiment of this specification, R1 and R2 are deuterium, and R3 and R4 are hydrogen.

[0127] In one embodiment of this specification, R1 and R2 are hydrogen, and R3 and R4 are deuterium.

[0128] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 carbon atoms.

[0129] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms.

[0130] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently represents a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted pyreneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted spirodifluoreneylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted furanylene, substituted or unsubstituted thiopheneylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted carbazolylene.

[0131] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, substituted or unsubstituted furanylene, or substituted or unsubstituted thiopheneylene.

[0132] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is directly bonded, phenylene, biphenylene, naphthylene, pyridylene, furanylene, or thiopheneylene.

[0133] In one embodiment of this specification, m is 0 or 1.

[0134] In one embodiment of this specification, n is 0 to 2.

[0135] In one embodiment of this specification, n is 0 or 1.

[0136] In one embodiment of this specification, X is S, O, or CR5R6, and R5 and R6 may be the same or different from each other, each being independently hydrogen, an alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or adjacent groups may combine with each other to form a ring with 3 to 30 substituted or unsubstituted carbon atoms.

[0137] In one embodiment of this specification, X is S, O, or CR5R6, and R5 and R6 may be the same or different from each other, each being independently hydrogen, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or adjacent groups may combine with each other to form a hydrocarbon ring having 3 to 30 carbon atoms.

[0138] In one embodiment of this specification, X is S, O, or CR5R6, and R5 and R6 may be the same or different from each other, each being independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms, or adjacent groups may combine with each other to form a hydrocarbon ring having 3 to 30 carbon atoms.

[0139] In one embodiment of this specification, X is S, O, or CR5R6, and R5 and R6 may be the same or different from each other, each being independently hydrogen, methyl, ethyl, propyl, butyl, phenyl, biphenyl, or naphthyl, or adjacent groups may combine with each other to form fluorene.

[0140] In one embodiment of this specification, X is S, O, or CR5R6, and R5 and R6 may be the same or different from each other, each being independently hydrogen, methyl, or phenyl, or adjacent groups may combine with each other to form a fluorene group.

[0141] In one embodiment of this specification, Z is an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms.

[0142] In one embodiment of this specification, Z is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0143] In one embodiment of this specification, Z is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with an alkyl group, or a heteroaryl group with 2 to 30 carbon atoms that is substituted or unsubstituted with an alkyl group.

[0144] In one embodiment of this specification, Z is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthryl, an alkyl-substituted or unsubstituted fluorenyl, a substituted or unsubstituted fluoranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted pyridyl, or a substituted or unsubstituted carbazoleyl.

[0145] In one embodiment of this specification, Z is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a methyl-substituted or unsubstituted fluorenyl, a substituted or unsubstituted fluoranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted pyridyl.

[0146] In one embodiment of this specification, Z is phenyl, biphenyl, naphthyl, phenanthryl, 9,9-dimethylfluorenyl, fluoranyl, dibenzofuranyl, dibenzothiopheneyl, or pyridyl.

[0147] In one embodiment of this specification, the compound of chemical formula 1 described above may be represented by any of the following compounds.

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] The compounds of Formula 1 described herein can be prepared with a core structure as shown in reactions 1 and 2 below. Substituents can be added by methods known in the art, and the type, position, and number of substituents can be varied according to techniques known in the art.

[0200] [Reaction Formula 1]

[0201]

[0202] [Reaction 2]

[0203]

[0204] In the above reaction formulas 1 and 2, Y1 to Y4, L1, R1 to R4, Z, G1 and G2 are defined as in the above chemical formula 2, and A is a halogen, preferably bromine or chlorine.

[0205] As shown above, in this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure. Furthermore, in this invention, the HOMO and LUMO energy levels of the compounds can also be tuned by introducing various substituents into the core structure shown above.

[0206] Furthermore, by introducing various substituents into the core structure shown above, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, by introducing the substituents primarily used in hole injection layer materials, hole transport materials, electron transport materials, electron suppression materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the aforementioned core structure, substances that meet the requirements of each organic layer can be synthesized.

[0207] Furthermore, the organic electronic device according to this specification is characterized by 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 a compound represented by the aforementioned chemical formula 1.

[0208] The organic electronic device described in this specification utilizes the aforementioned compound to form one or more organic layers. Alternatively, it can be manufactured using conventional organic electronic device manufacturing methods and materials.

[0209] In one embodiment of the present invention, the organic electronic device may be selected from organic light-emitting devices, organic phosphorescent devices, organic solar cells, organic photosensitive cells (OPC), and organic transistors.

[0210] The following is an example of an organic light-emitting device.

[0211] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0212] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device described in this specification may have a structure comprising a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer, as well as a layer that simultaneously performs electron transport and electron injection, etc., as organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0213] In the organic light-emitting device described in this specification, the organic layer may include an electron injection layer, which may contain the compounds mentioned above.

[0214] In the organic light-emitting device described in this specification, the organic layer may include an electron transport layer, which may contain the compounds mentioned above.

[0215] In the organic light-emitting device described in this specification, the organic layer includes a light-emitting layer, which contains the compounds mentioned above.

[0216] According to another embodiment, the organic layer includes a light-emitting layer, which may contain the aforementioned compound as a dopant for the light-emitting layer.

[0217] In another embodiment, the organic layer includes a light-emitting layer, which contains the aforementioned compound as a dopant for the light-emitting layer, and may also include a host.

[0218] In another embodiment, the organic layer includes a light-emitting layer containing the aforementioned compound as a dopant, and may contain a fluorescent host or a phosphorescent host, and may contain other organic compounds, metals or metal compounds as dopant.

[0219] As another example, the organic layer described above includes a light-emitting layer containing the aforementioned compound as a dopant, comprising a fluorescent host or a phosphorescent host, which can be used in conjunction with iridium (Ir) dopants.

[0220] According to another embodiment, the organic layer includes a light-emitting layer, which may contain the aforementioned compound as the main body of the light-emitting layer.

[0221] As another example, the aforementioned organic layer includes a light-emitting layer, which contains the aforementioned compound as the main body of the light-emitting layer, and may also contain dopants.

[0222] As another example, the aforementioned organic layer includes a light-emitting layer, which contains the aforementioned compound as the main body of the light-emitting layer and may also contain a dopant. The content of the dopant relative to 100 parts by weight of the main body may be from 1 part by weight to 20 parts by weight, more preferably from 1 part by weight to 5 parts by weight.

[0223] In the organic light-emitting device described in this specification, the organic layer includes an electron blocking layer, which may contain the aforementioned compound.

[0224] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0225] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0226] For example, the organic light-emitting devices described above can have the layered structure described below, but are not limited to this.

[0227] (1) Anode / hole transport layer / light-emitting layer / cathode

[0228] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0229] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0230] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0231] (5) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0232] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Injection and Transport Layer / Cathode

[0233] (7) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0234] (8) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0235] (9) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0236] (10) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0237] (11) Anode / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Cathode

[0238] (12) Anode / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Electron injection layer / Cathode

[0239] (13) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Cathode

[0240] (14) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0241] (15) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Hole suppression layer / Layer that performs both electron injection and electron transport simultaneously / Cathode

[0242] The organic light-emitting device structure described in this specification can have the following characteristics: Figure 1 and Figure 2 The structure shown is not limited to this.

[0243] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the aforementioned compound may be included in the light-emitting layer 3.

[0244] Figure 2 The diagram 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 light-emitting layer 7, a layer 8 that simultaneously performs electron injection and electron transport, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the aforementioned compound may be contained in the hole injection layer 5, the hole transport layer 6, the light-emitting layer 7, or the layer 8 that simultaneously performs electron injection and electron transport.

[0245] For example, the organic light-emitting device according to the present invention can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a hole suppression layer, and a layer that simultaneously performs electron transport and electron injection is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0246] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a hole suppression layer, a layer that simultaneously performs electron injection and electron transport, an electron blocking layer, a light-emitting layer, and layers that simultaneously perform electron injection and hole transport, but it is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0247] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this 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), 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-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0248] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the 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 their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0249] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltage. Preferably, 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, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0250] The aforementioned hole transport layer facilitates hole transport. Hole transport materials are substances capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; substances with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0251] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. This electron blocking layer prevents holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, thereby improving the device's lifetime and efficiency. The aforementioned compound or materials known in this technical field may be used.

[0252] The aforementioned light-emitting layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent materials. The aforementioned light-emitting material is capable of receiving holes and electrons from the hole transport layer and electron transport layer respectively, and combining them to emit light in the visible light region; preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. When the aforementioned organic light-emitting device includes a light-emitting layer other than the one containing a compound represented by the aforementioned chemical formula 1, the additional light-emitting layer can emit red, green, or blue light and can be composed of phosphorescent or fluorescent materials. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0253] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0254] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the luminescent layer emits green light, phosphorescent dopants such as Ir(ppy)3 (facilitated tris(2-phenylpyridine)iridium) or fluorescent dopants such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used, but are not limited to these. When the luminescent layer emits blue light, phosphorescent dopants such as (4,6-F2ppy)2Irpic or fluorescent dopants such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, PPV-based polymers, etc., can be used, but are not limited to these.

[0255] A hole suppression layer can be disposed between the electron transport layer and the light-emitting layer. This hole suppression layer is designed to prevent holes from reaching the cathode and can typically be formed under the same conditions as the hole injection layer. Specifically, hole suppression materials include triazine derivatives, phenanthroline derivatives, BCP, etc., but are not limited to these; materials known in this art can be used.

[0256] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 nm to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing the driving voltage from increasing to improve electron migration when the electron transport layer is too thick.

[0257] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the luminescent layer or luminescent material, prevent excitons generated in the luminescent layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0258] The layer mentioned above that performs both electron injection and electron transport refers to a layer that simultaneously functions as both an electron injection layer and an electron transport layer.

[0259] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, 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, but are not limited to these.

[0260] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0261] Methods of implementing the invention

[0262] The following examples will be provided to illustrate this specification in detail. However, the embodiments described in this specification can be modified in various ways and should not be construed as limiting the scope of this application to the embodiments detailed below. The embodiments of this application are provided to provide a more complete explanation of this specification to those skilled in the art.

[0263] Manufacturing Example 1-1 <Preparation of Compound C1>

[0264]

[0265] Under a nitrogen atmosphere, compound P1-A (41.0 g, 108.9 mmol) and compound S (27.7 g, 108.9 mmol) were added to 500 mL of tetrahydrofuran and stirred. Then, potassium carbonate (15.8 g, 114.3 mmol) dissolved in 65 mL of water was added and stirred thoroughly. Next, [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (Pd(dppf)Cl2, 0.16 g, 0.218 mmol) was added. The mixture was then slowly heated and refluxed for 7 hours, followed by cooling to room temperature. The organic and aqueous layers were then separated, and the resulting solid was filtered. The filtered solid was dissolved in toluene at 100 °C, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate and acidic clay were added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was then distilled under reduced pressure. The concentrated solid was filtered, refluxed in 10 times its volume of tetrahydrofuran, and stirred for 1 hour. After cooling to room temperature and filtering, a white solid compound P1 (43.8 g, 73%, MS: [M+H)) was produced. + =552).

[0266]

[0267] Under a nitrogen atmosphere, compound P1 (21.6 g, 39.2 mmol) and compound A1 (14.3 g, 117.6 mmol) were added to 1000 mL of toluene and stirred. Then, potassium carbonate (16.2 g, 117.6 mmol) dissolved in 100 mL of water was added, and after thorough stirring, [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (0.14 g, 0.02 mmol) was added. The mixture was then slowly heated and refluxed for 12 hours, after which it was cooled to room temperature. 500 mL of toluene was distilled, and after cooling to room temperature, the resulting solid was filtered. The filtered solid was dissolved in toluene at 90 °C, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate, acidic clay, and activated carbon were added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated solid was filtered and recrystallized from tetrahydrofuran and ethyl acetate to produce a white solid compound C1 (15.2 g, 66%, MS: [M+H)). + =593).

[0268] Manufacturing Examples 1-2: <Manufacturing of Compound C2>

[0269]

[0270] The starting materials were used as described in the above reaction formula, except that the above compound C2 was manufactured by the same method as that used in manufacturing example 1-1.

[0271] MS:[M+H] + =669

[0272] Manufacturing Examples 1-3: <Manufacturing of Compound C3>

[0273]

[0274] The starting materials were used as described in the above reaction formula, except that the above compound C3 was manufactured by the same method as that used in manufacturing example 1-1.

[0275] MS:[M+H] + =669

[0276] Manufacturing Examples 1-4: <Manufacturing of Compound C4>

[0277]

[0278] The starting materials were used as described in the above reaction formula, except that the above compound C4 was manufactured by the same method as that used in manufacturing example 1-1.

[0279] MS:[M+H] + =719

[0280] Manufacturing Examples 1-5: <Manufacturing of Compound C5>

[0281]

[0282] The starting materials were used as described in the above reaction formula, except that the above compound C5 was manufactured by the same method as that used in manufacturing example 1-1.

[0283] MS:[M+H] + =719

[0284] Manufacturing Examples 1-6: <Manufacturing of Compound C6>

[0285]

[0286] The starting materials were used as described in the above reaction formula, except that the above compound C6 was manufactured by the same method as that used in manufacturing example 1-1.

[0287] MS:[M+H] + =709

[0288] Manufacturing Examples 1-7: <Manufacturing of Compound C7>

[0289]

[0290] The starting materials were used as described in the above reaction formula, except that the above compound C7 was manufactured by the same method as that used in manufacturing example 1-1.

[0291] MS:[M+H] + =669

[0292] Manufacturing Examples 1-8: <Manufacturing of Compound C8>

[0293]

[0294] The starting materials were used as described in the above reaction formula, except that the above compound C8 was manufactured by the same method as that used in manufacturing example 1-1.

[0295] MS:[M+H] + =745

[0296] Manufacturing Examples 1-9: <Manufacturing of Compound C9>

[0297]

[0298] The starting materials were used as described in the above reaction formula, except that the above compound C9 was manufactured by the same method as that used in manufacturing example 1-1.

[0299] MS:[M+H] + =795

[0300] Manufacturing Examples 1-10: <Manufacturing of Compound C10>

[0301]

[0302] The starting materials were used as described in the above reaction formula, except that the above compound C10 was manufactured by the same method as that used in manufacturing example 1-1.

[0303] MS:[M+H] + =759

[0304] Manufacturing Examples 1-11: <Manufacturing of Compound C11>

[0305]

[0306] The starting materials were used as described in the above reaction formula, except that the above compound C11 was manufactured by the same method as that used in manufacturing example 1-1.

[0307] MS:[M+H] + =669

[0308] Manufacturing Examples 1-12: <Manufacturing of Compound C12>

[0309]

[0310] The starting materials were used as described in the above reaction formula, except that the above compound C12 was manufactured by the same method as that used in manufacturing example 1-1.

[0311] MS:[M+H] + =745

[0312] Manufacturing Examples 1-13: <Manufacturing of Compound C13>

[0313]

[0314] The starting materials were used as described in the above reaction formula, except that the above compound C13 was manufactured by the same method as that used in manufacturing example 1-1.

[0315] MS:[M+H] + =745

[0316] Manufacturing Examples 1-14: <Manufacturing of Compound C14>

[0317]

[0318] The starting materials were used as described in the above reaction formula, except that the above compound C14 was manufactured by the same method as that used in manufacturing example 1-1.

[0319] MS:[M+H] + =795

[0320] Manufacturing Examples 1-15: <Manufacturing of Compound C15>

[0321]

[0322] The starting materials were used as described in the above reaction formula, except that the above compound C15 was manufactured by the same method as that used in manufacturing example 1-1.

[0323] MS:[M+H] + =669

[0324] Manufacturing Examples 1-16: <Manufacturing of Compound C16>

[0325]

[0326] The starting materials were used as described in the above reaction formula, except that the above compound C16 was manufactured by the same method as that used in manufacturing example 1-1.

[0327] MS:[M+H] + =745

[0328] Manufacturing Examples 1-17: <Manufacturing of Compound C17>

[0329]

[0330] The starting materials were used as described in the above reaction formula, except that the above compound C17 was manufactured by the same method as that used in manufacturing example 1-1.

[0331] MS:[M+H] + =795

[0332] Manufacturing Examples 1-18: <Manufacturing of Compound C18>

[0333]

[0334] The starting materials were used as described in the above reaction formula, except that the above compound C18 was manufactured by the same method as that used in manufacturing example 1-1.

[0335] MS:[M+H] + =745

[0336] Manufacturing Example 1-19: <Manufacturing of Compound C19>

[0337]

[0338] The starting materials were used as described in the above reaction formula, except that the above compound C19 was manufactured by the same method as that used in manufacturing example 1-1.

[0339] MS:[M+H] + =745

[0340] Manufacturing Examples 1-20: <Manufacturing of Compound C20>

[0341]

[0342] The starting materials were used as described in the above reaction formula, except that the above compound C20 was manufactured by the same method as that used in manufacturing example 1-1.

[0343] MS:[M+H] + =795

[0344] Manufacturing Example 1-21: <Manufacturing of Compound C21>

[0345]

[0346] The starting materials were used as described in the above reaction formula, except that the above compound C21 was manufactured by the same method as that used in manufacturing example 1-1.

[0347] MS:[M+H] + =745

[0348] Manufacturing Example 1-22: <Manufacturing of Compound C22>

[0349]

[0350] The starting materials were used as described in the above reaction formula, except that the above compound C22 was manufactured by the same method as that used in manufacturing example 1-1.

[0351] MS:[M+H] + =669

[0352] Manufacturing Example 1-23: <Manufacturing of Compound C23>

[0353]

[0354] The starting materials were used as described in the above reaction formula, except that the above compound C23 was manufactured by the same method as that used in manufacturing example 1-1.

[0355] MS:[M+H] + =669

[0356] Manufacturing Examples 1-24: <Manufacturing of Compound C24>

[0357]

[0358] The starting materials were used as described in the above reaction formula, except that the above compound C24 was manufactured by the same method as that used in manufacturing example 1-1.

[0359] MS:[M+H] + =795

[0360] Manufacturing Example 1-25: <Manufacturing of Compound C25>

[0361]

[0362] The starting materials were used as described in the above reaction formula, except that the above compound C25 was manufactured by the same method as that used in manufacturing example 1-1.

[0363] MS:[M+H] + =745

[0364] Manufacturing Example 1-26: <Preparation of Compound C26>

[0365]

[0366] The starting materials were used as described in the above reaction formula, except that the above compound C26 was manufactured by the same method as that used in manufacturing example 1-1.

[0367] MS:[M+H] + =795

[0368] Manufacturing Example 1-27: <Manufacturing of Compound C27>

[0369]

[0370] The starting materials were used as described in the above reaction formula, except that the above compound C27 was manufactured by the same method as that used in manufacturing example 1-1.

[0371] MS:[M+H] + =670

[0372] Manufacturing Example 1-28: <Manufacturing of Compound C28>

[0373]

[0374] The starting materials were used as described in the above reaction formula, except that the above compound C28 was manufactured by the same method as that used in manufacturing example 1-1.

[0375] MS:[M+H] + =679

[0376] Manufacturing Example 1-29: <Manufacturing of Compound C29>

[0377]

[0378] The starting materials were used as described in the above reaction formula, except that the above compound C29 was manufactured by the same method as that used in manufacturing example 1-1.

[0379] MS:[M+H] + =643

[0380] Manufacturing Examples 1-30: <Manufacturing of Compound C30>

[0381]

[0382] The starting materials were used as described in the above reaction formula, except that the above compound C30 was manufactured by the same method as that used in manufacturing example 1-1.

[0383] MS:[M+H] + =670

[0384] Manufacturing Example 1-31: <Manufacturing of Compound C31>

[0385]

[0386] The starting materials were used as described in the above reaction formula, except that the above compound C31 was manufactured by the same method as that used in manufacturing example 1-1.

[0387] MS:[M+H] + =647

[0388] Example 1-1

[0389] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0390] On the ITO transparent electrode prepared in this way, the following compound [HI-A] is applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On this hole injection layer, hexanitrile hexaazabenzophenanthrene (HAT) with the following chemical formula is sequentially vacuum-deposited. And the following compound [HT-A] This forms a hole transport layer.

[0391] Next, on the aforementioned hole transport layer, with a film thickness... A light-emitting layer was formed by vacuum evaporation of the following compounds [BH] and [BD] in a weight ratio of 25:1.

[0392] On the aforementioned light-emitting layer, the above-mentioned compound C1 and the following compound [LiQ] (lithium quinolate) were vacuum-deposited in a 1:1 weight ratio to achieve the desired effect. A layer with a thickness sufficient for simultaneous electron injection and electron transport is formed. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0393] During the above process, the evaporation rate of the organic matter is maintained at 0.4 to... / second, lithium fluoride at the cathode maintains Evaporation rate of / second, aluminum maintains A vapor deposition rate of / second is achieved, while maintaining a vacuum level of 1×10⁻⁶ during vapor deposition. -7 Up to 5×10 -8 This led to the creation of organic light-emitting devices.

[0394]

[0395] Examples 1-2 to 1-31

[0396] In Examples 1-1 above, the compounds listed in Table 1 below were used instead of compound C1. Otherwise, the organic light-emitting device was manufactured using the same method as in Examples 1-1.

[0397] Comparative Examples 1-1 to 1-7

[0398] In Examples 1-1 above, the compounds listed in Table 1 below were used instead of compound C1. Otherwise, the organic light-emitting device was manufactured using the same method as in Examples 1-1.

[0399]

[0400] For organic light-emitting devices at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T0) at the current density relative to the initial brightness was measured to reach 90%. 90 The results are shown in Table 1 below.

[0401] [Table 1]

[0402]

[0403]

[0404] As shown in Table 1 above, the compounds represented by chemical formula 1 according to this specification can be used in organic layers of organic light-emitting devices that can simultaneously perform electron injection and electron transport.

[0405] Comparing Examples 1-1 to 1-31 in Table 1 above with Comparative Examples 1-1 to 1-3, it can be confirmed that when using compounds combining chemical formulas 1 and 2 according to this specification, organic light-emitting devices exhibit significantly superior characteristics in terms of efficiency and lifetime compared to organic light-emitting devices containing triazine in chemical formula 1.

[0406] Comparing Examples 1-1 to 1-31 in Table 1 above with Comparative Examples 1-4 to 1-7, it can be confirmed that organic light-emitting devices containing compounds of chemical formula 1 and chemical formula 2 according to this specification exhibit significantly superior characteristics in terms of efficiency and lifetime compared to organic light-emitting devices containing benzothiophenepyridine, or benzothiophenetriazine, or compounds substituted with two or more chemical formulas 2, or compounds with benzene rings fused in the core structure of chemical formula 1, which are different from chemical formula 2 of the present invention.

Claims

1. An organic electronic device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein the organic layer includes an electron injection and transport layer, and the electron injection and transport layer comprises a compound of chemical formula 1 and a metal coordination compound: Chemical Formula 1 In the chemical formula 1, G1 and G2 are hydrogen, or can be represented by the following chemical formulas 2-9. a is an integer from 1 to 8. b is an integer from 1 to 8. When G1 is represented by chemical formula 2-9, G2 is hydrogen and a is 1. When G1 is hydrogen, G2 is represented by chemical formula 2-9 and b is 1. Chemical formula 2-9 In the chemical formulas 2-9, R1 to R4 may be the same as or different from each other, and each can be hydrogen or deuterium independently. L1 and L2 may be the same or different from each other, and each is independently a directly bonded arylene with 6 to 30 carbon atoms, or a heteroarylene with 2 to 30 carbon atoms. X is S, O, or CR5R6. R5 and R6 may be the same as or different from each other, and each is independently an alkyl group having 1 to 20 carbon atoms. m is an integer of 0 or 1. The n is an integer from 0 to 2. Z is an aryl group with 6 to 30 carbon atoms that is substituted with or unsubstituted with an alkyl group having 1 to 20 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms. The asterisk (*) indicates the position where it combines with chemical formula 1. The metal coordination compound is selected from one or more of the following: lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, 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, and bis(2-methyl-8-quinoline)(2-naphthol)gallium.

2. The organic electronic device according to claim 1, wherein, The L1 and L2 may be the same as or different from each other, and each independently can be directly bonded, phenylene, biphenylene, naphthylene, anthracene, phenanthrene, pyrene, fluorene, spirodifluorene, pyridinyl, pyrimidinyl, furanyl, thiophene, dibenzofuranyl, or carbazolyl.

3. The organic electronic device according to claim 1, wherein, Z is phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl (substituted or unsubstituted with methyl), fluoranyl, dibenzofuranyl, dibenzothiopheneyl, or pyridyl.

4. The organic electronic device according to claim 1, wherein, The compound of chemical formula 1 is any one of the following compounds:

5. The organic electronic device according to claim 1, wherein, The organic electronic devices are selected from organic light-emitting devices, organic phosphorescent devices, organic solar cells, organic photosensitive cells (OPC), and organic transistors.

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