Organic light-emitting devices containing organic compounds

Abstract

This specification relates to organic light-emitting devices that include a light-emitting layer.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2020-0134369, filed with the Korean Patent Office on October 16, 2020, the entire contents of which are contained in this specification.

[0002] This specification relates to organic light-emitting devices that contain organic compounds. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with 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, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.

[0005] Existing technical documents

[0006] (Patent Document 1) Patent Publication No. 10-2015-0011347 Summary of the Invention

[0007] Technical issues

[0008] This specification provides organic light-emitting devices that contain organic compounds.

[0009] Solution to the problem

[0010] This specification provides an organic light-emitting device, comprising:

[0011] Anode, cathode, and an organic layer disposed between the anode and the cathode.

[0012] The aforementioned organic layer includes a light-emitting layer.

[0013] The maximum emission peak of the aforementioned light-emitting layer exists in the range of 400 nm to 500 nm.

[0014] The aforementioned luminescent layer comprises a compound of chemical formula 1 and a compound of chemical formula 2.

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] Ar1 can be a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthyl group.

[0019] L1 is a directly bonded, substituted, or unsubstituted aryl group.

[0020] X1 is either O or S.

[0021] One of R1 to R8 is attached to L1, and the others may be the same as or different from each other. Each of them is independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, or combined with adjacent substituents to form a substituted or unsubstituted ring.

[0022] n1 is an integer from 0 to 3.

[0023] [Chemical Formula 2]

[0024]

[0025] In the above chemical formula 2,

[0026] D stands for deuterium.

[0027] Ar11 and Ar12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0028] Ar13 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0029] L11 and L12 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group.

[0030] m1 is an integer from 0 to 7.

[0031] Invention Effects

[0032] The organic light-emitting device described in this specification exhibits low driving voltage, excellent efficiency characteristics, and excellent lifetime by including compounds of Formula 1 and Formula 2 in the light-emitting layer. Specifically, by appropriately adjusting the HOMO and LUMO energy levels to regulate electron and hole transport, a lower driving voltage, higher efficiency, and improved lifetime can be achieved.

[0033] In particular, Formula 1 has a higher triplet energy level, which can show additional efficiency gains through an additional electron transfer mechanism based on the triplet state. Attached Figure Description

[0034] Figure 1 and 2 An example of an organic light-emitting device according to one embodiment of this specification is illustrated. Detailed Implementation

[0035] The following is a more detailed description of this instruction manual.

[0036] The present invention comprises a structure in which a dibenzofuran or dibenzothiophene is attached to a polycyclic aryl group of phenanthrene, pyrene, triphenylene, or fluoranthracene. When a compound of formula 1 is used as the host of a blue luminescent layer, an additional efficiency enhancement effect can be observed by utilizing the significantly higher triplet energy level compared to an anthracene-based host through electron migration to the triplet energy level of the dopant.

[0037] The anthracene compound of this invention, chemical formula 2, exhibits excellent electron and hole migration and injection, but its energy efficiency is low due to fluorescence emission via singlet energy levels. When the blue emitting layer comprises both the compound of chemical formula 1 and the compound of chemical formula 2, the additional efficiency increase effect of the compound of chemical formula 1 can be obtained while maintaining stable performance through appropriate energy levels and electron / hole balance of the anthracene compound of chemical formula 2.

[0038] In this specification, * or dashed lines indicate connection points.

[0039] In this specification, Cn refers to a number of n carbon atoms, and Cn-Cm refers to a number of n to m carbon atoms.

[0040] Examples of substituents in this specification are described below, but are not limited thereto.

[0041] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in 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 more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0042] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano, alkyl, cycloalkyl, silyl, aryl, and heterocyclic groups, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0043] In this specification, "two or more substituents linked" means that the hydrogen of any one substituent is linked to other substituents. For example, isopropyl can be linked to phenyl to form... Such substituents.

[0044] In this specification, the connection of three substituents includes not only a continuous connection of (substituent 1)-(substituent 2)-(substituent 3), but also a connection of (substituent 2) and (substituent 3) within (substituent 1). For example, the connection of two phenyl groups and an isopropyl group can form... Such substituents. The same definition applies to cases where four or more substituents are connected.

[0045] In one embodiment of this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, C1-C10 alkyl groups, C3-C30 cycloalkyl groups, silyl groups, C6-C30 aryl groups, and C2-C30 heterocyclic groups, or substituted by or unsubstituted by substituents formed by connecting two or more substituents selected from the above group.

[0046] In one embodiment of this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, C1-C6 alkyl groups, C3-C20 cycloalkyl groups, silyl groups, C6-C20 aryl groups, and C2-C20 heterocyclic groups, or substituted by or unsubstituted by substituents formed by connecting two or more substituents selected from the above group.

[0047] In this specification, N% deuteration means that N% of the usable hydrogens in the structure are replaced by deuterium. For example, in dibenzofuran, 25% deuteration means that 2 out of the 8 hydrogens in dibenzofuran are replaced by deuterium.

[0048] Compounds containing deuterium of formula 1 or 2 can be produced by known deuteration reactions. According to one embodiment of this specification, compounds of formula 1 are formed by using a deuterated compound as a precursor, or deuterium can be introduced into the compound via a hydrogen-deuterium exchange reaction using a deuterated solvent and an acid catalyst.

[0049] In this specification, the degree of deuteration can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 Confirmation is performed using known methods such as H NMR or GC / MS.

[0050] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0051] In this specification, alkyl groups can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0052] In this specification, aryl refers to a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. An aromatic hydrocarbon is a planar ring compound containing fully conjugated π electrons, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is fused together. Furthermore, in this specification, aryl includes a monovalent group formed by the linkage of two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives. There is no particular limitation on the aryl group, but it is preferably an aryl group with 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the aforementioned aryl group can be monocyclic or polycyclic. Specifically, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. Polycyclic aryl groups can be naphthyl, anthraceneyl, phenanthryl, triphenyl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0053] In this specification, the fluorene group can be substituted, and adjacent substituents can combine with each other to form a ring.

[0054] In this specification, when it is indicated that the fluorene group can be substituted, all compounds in which the substituents of the five-membered ring of fluorene are spirolinked together to form an aromatic hydrocarbon ring are included. The aforementioned substituted fluorene groups include, but are not limited to, 9,9'-spirodifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc.

[0055] In this specification, the substituted aryl group may include a form in which an aliphatic ring is fused to the aryl group.

[0056] In this specification, a heterocyclic group refers to a monovalent aromatic heterocycle. Here, an aromatic heterocycle, as a monovalent group of an aromatic ring or a derivative of an aromatic ring, refers to a group containing one or more of N, O, and S as heteroatoms within the ring. The aforementioned derivatives of aromatic rings include all structures in which aromatic rings or aliphatic rings are fused together. Furthermore, in this specification, a heterocyclic group comprises a monovalent group formed by the interconnection of two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms. The number of carbon atoms in the aforementioned heterocyclic group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. Azolyl, pyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] The group includes, but is not limited to, azole, benzimidazole, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, benzofuran, phenanthrolinel, and dibenzofuran.

[0057] In this specification, the heterocyclic group can be monocyclic or polycyclic, and can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds.

[0058] In this specification, cycloalkyl groups are not particularly limited, but are preferably cycloalkyl groups 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 yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cycloalkyl groups include not only monocyclic groups, but also bicyclic groups such as bridgeheads, fused rings, and spiro groups. Specifically, they include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited to these.

[0059] In this specification, aliphatic hydrocarbon rings refer to all hydrocarbon rings other than aromatic hydrocarbon rings, and may include cycloalkyl rings and cycloalkenyl rings. The descriptions regarding cycloalkyl groups, except that they are divalent groups, are applicable to cycloalkyl rings, and the descriptions regarding cycloalkenyl groups, except that they are divalent groups, are applicable to cycloalkenyl rings. Furthermore, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0060] In this specification, arylene refers to a group with two bonding positions in 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.

[0061] In this specification, a heteroaryl group refers to a group with two bonding positions in a heterocyclic group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heterocyclic groups.

[0062] An organic light-emitting device according to one embodiment of this specification includes:

[0063] Anode, cathode, and an organic layer disposed between the anode and the cathode.

[0064] The aforementioned organic layer includes a light-emitting layer.

[0065] The maximum emission peak of the aforementioned light-emitting layer exists in the range of 400 nm to 500 nm.

[0066] The aforementioned luminescent layer comprises a compound of chemical formula 1 and a compound of chemical formula 2.

[0067] [Chemical Formula 1]

[0068]

[0069] In the above chemical formula 1,

[0070] Ar1 can be a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthyl group.

[0071] L1 is a directly bonded, substituted, or unsubstituted aryl group.

[0072] X1 is either O or S.

[0073] One of R1 to R8 is attached to L1, and the others may be the same as or different from each other. Each of them is independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, or combined with adjacent substituents to form a substituted or unsubstituted ring.

[0074] n1 is an integer from 0 to 3.

[0075] [Chemical Formula 2]

[0076]

[0077] In the above chemical formula 2,

[0078] D stands for deuterium.

[0079] Ar11 and Ar12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0080] Ar13 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0081] L11 and L12 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group.

[0082] m1 is an integer from 0 to 7.

[0083] The compounds of chemical formula 1 will now be described in detail.

[0084] In one embodiment of this specification, Ar1 is a substituted or unsubstituted phenanthrene, a substituted or unsubstituted pyrene, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted fluoranthyl.

[0085] In one embodiment of this specification, Ar1 is a phenanthrene group that is deuterated or unsubstituted, a pyrene group that is deuterated or unsubstituted, a triphenylene group that is deuterated or unsubstituted, or a fluoranthyl group that is deuterated or unsubstituted.

[0086] In one embodiment of this specification, Ar1 is phenanthrene, pyrene, triphenylene, or fluoranthyl.

[0087] In one embodiment of this specification, Ar1 is any one of the following chemical formulas PAr1 to PAr4.

[0088] [Chemical formula PAr1]

[0089]

[0090] [Chemical formula PAr2]

[0091]

[0092] [Chemical formula PAr3]

[0093]

[0094] [Chemical formula PAr4]

[0095]

[0096] In the above chemical formulas PAr1 to PAr4,

[0097] The dashed line represents the part that connects to L1 in the above chemical formula 1.

[0098] G1 to G7 may be the same or different, and each is independently a hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0099] g1 and g7 are integers from 0 to 3, g2 is an integer from 0 to 8, g3 is an integer from 0 to 9, g4 is an integer from 0 to 4, g5 is an integer from 0 to 5, and g6 is an integer from 0 to 6.

[0100] When g1 to g7 are each 2 or more, the substituents in the parentheses may be the same or different from each other.

[0101] In one embodiment of this specification, G1 to G7 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0102] In one embodiment of this specification, G1 to G7 are hydrogen.

[0103] In one embodiment of this specification, the above-mentioned chemical formula PAr1 is the following chemical formula PAr1-1.

[0104] [Chemical formula PAr1-1]

[0105]

[0106] In the above chemical formula PAr1-1,

[0107] The dashed lines, G1, G2, g1, and g2 are defined in the same way as those in the above chemical formula PAr1.

[0108] In one embodiment of this specification, the above-mentioned chemical formula PAr2 is the following chemical formula PAr2-1.

[0109] [Chemical formula PAr2-1]

[0110]

[0111] In the above chemical formula PAr2-1,

[0112] The dashed line, G3, and g3 are defined in the above chemical formula PAr2.

[0113] In one embodiment of this specification, the above-mentioned chemical formula PAr3 is the following chemical formula PAr3-1.

[0114] [Chemical formula PAr3-1]

[0115]

[0116] In the above chemical formula PAr3-1,

[0117] The dashed lines, G4, G5, g4, and g5 are defined in the above chemical formula PAr3.

[0118] In one embodiment of this specification, the above-mentioned chemical formula PAr4 is the following chemical formula PAr4-1.

[0119] [Chemical formula PAr4-1]

[0120]

[0121] In the above chemical formula PAr4-1,

[0122] The dashed lines, G6, G7, g6, and g7 are defined in the above chemical formula PAr4.

[0123] In one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted C6-C30 aryl group.

[0124] In one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted C6-C20 aryl group.

[0125] In one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted C6-C10 aryl group.

[0126] In one embodiment of this specification, L1 is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0127] In one embodiment of this specification, L1 is a directly bonded, deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenylene, or a deuterated or unsubstituted naphthylene.

[0128] In one embodiment of this specification, L1 is a direct bond, a phenylene group, or a naphthylene group.

[0129] In one embodiment of this specification, L1 is a direct bond.

[0130] In one embodiment of this specification, L1 is a direct bond or selected from any of the following structures.

[0131]

[0132] In the above structure,

[0133] The dashed line represents the part that connects to the above chemical formula 1.

[0134] The above structure is substituted or unsubstituted by deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups.

[0135] In one embodiment of this specification, the above structure may or may not be replaced by deuterium.

[0136] In one embodiment of this specification, n1 is 0 or 1.

[0137] In one embodiment of this specification, X1 is 0.

[0138] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, or combined with an adjacent substituent to form a substituted or unsubstituted ring.

[0139] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others may be the same as or different from each other, each being independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C90 arylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, or combined with an adjacent substituent to form a substituted or unsubstituted C5-C30 ring.

[0140] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others may be the same as or different from each other, each being independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C18 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heterocyclic group, or combined with an adjacent substituent to form a substituted or unsubstituted C5-C20 ring.

[0141] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others may be the same as or different from each other, each being independently hydrogen, deuterium, or a substituted or unsubstituted C6-C20 aryl group, or two adjacent substituents may be bonded together to form a substituted or unsubstituted C5-C20 ring. In this case, the two adjacent substituents refer to R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8.

[0142] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, or a substituted or unsubstituted C6-C10 aryl group, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are combined with each other to form a substituted or unsubstituted benzene ring.

[0143] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are combined with each other to form a substituted or unsubstituted benzene ring.

[0144] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted 1-naphthyl, or substituted or unsubstituted 2-naphthyl, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are combined with each other to form a substituted or unsubstituted benzene ring.

[0145] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are combined with each other to form a deuterated or unsubstituted benzene ring.

[0146] In one embodiment of this specification, one of R1 to R8 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, phenyl, biphenyl or naphthyl, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are combined with each other to form a benzene ring.

[0147] In one embodiment of this specification, one or more of R1 to R8 are substituted or unsubstituted aryl groups.

[0148] In one embodiment of this specification, one or more of R1 to R8 are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0149] In one embodiment of this specification, (L1) n1 In the case of direct bonding, one or more of R1 to R8 are substituted or unsubstituted aryl groups.

[0150] In one embodiment of this specification, (L1) n1 When the bonding is direct, one or more of R1 to R8 are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0151] In one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following chemical formulas 101 to 103.

[0152] [Chemical Formula 101]

[0153]

[0154] [Chemical Formula 102]

[0155]

[0156] [Chemical Formula 103]

[0157]

[0158] In the above chemical formulas 101 to 103,

[0159] Ar1, L1, and n1 are defined in the same way as in chemical formula 1 above.

[0160] One of R1 to R12 is connected to L1, and the rest are the same as or different from each other, and are independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group.

[0161] In one embodiment of this specification, any one of R1 to R12 is connected to L1, and the others are the same as or different from each other, each being independently hydrogen, deuterium, or a substituted or unsubstituted C6-C20 aryl group.

[0162] In one embodiment of this specification, any one of R1 to R12 is connected to L1, and the others are the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0163] In one embodiment of this specification, any one of R1 to R12 is connected to L1, and the others are the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted 1-naphthyl, or substituted or unsubstituted 2-naphthyl.

[0164] In one embodiment of this specification, one or more of R1 to R12 are substituted or unsubstituted aryl groups.

[0165] In one embodiment of this specification, one or more of R1 to R12 are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0166] In one embodiment of this specification, one of R1 to R12 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl, and the remainder is hydrogen or deuterium.

[0167] In one embodiment of this specification, (L1) n1 When the bonding is direct, one or more of R1 to R12 are substituted or unsubstituted aryl groups.

[0168] In one embodiment of this specification, (L1) n1 When the bonding is direct, one or more of R1 to R12 are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0169] In one embodiment of this specification, (L1) n1 When the bonding is direct, one of R1 to R12 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl group, and the remainder is hydrogen or deuterium.

[0170] In one embodiment of this specification, R1 is connected to L1. In another embodiment, R2 is connected to L1. In another embodiment, R3 is connected to L1. In another embodiment, R4 is connected to L1. In another embodiment, R5 is connected to L1. In another embodiment, R6 is connected to L1. In another embodiment, R7 is connected to L1. In another embodiment, R8 is connected to L1. In another embodiment, R9 is connected to L1. In another embodiment, R10 is connected to L1. In another embodiment, R11 is connected to L1. In another embodiment, R12 is connected to L1.

[0171] In one embodiment of this specification, the above-mentioned chemical formula 1 is selected from one of the following compounds.

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185] The light-emitting layer of an organic light-emitting device according to one embodiment of this specification comprises a compound of chemical formula 1 and a compound of chemical formula 2.

[0186] In one embodiment of this specification, the triplet energy level (T1) of the compound of chemical formula 1 is higher than that of the compound of chemical formula 2.

[0187] In one embodiment of this specification, the triplet energy level (T1) of the compound of Formula 1 is 2.0 eV or higher. Preferably, it is 2.01 eV or higher.

[0188] In another embodiment, the triplet energy level (T1) of the compound of Formula 1 is 3.0 eV or less. Preferably, it is 2.9 eV or less, and more preferably 2.8 eV or less.

[0189] The triplet energy level of the compound of chemical formula 1 is higher than that of the compound of chemical formula 2. When the above range is satisfied, it is easy to inject electrons into the triplet energy level of the dopant, thereby increasing the exciton formation ratio and having the advantage of improving luminescence efficiency.

[0190] In this specification, the triplet level (T1) can be measured using a spectrometer capable of measuring fluorescence and phosphorescence. For the measurement conditions, a concentration of 10 is prepared using toluene or tetrahydrofuran (THF) as a solvent under extremely low temperatures with liquefied nitrogen. -6 When a solution of M is irradiated with a light source within the absorption wavelength range of the substance, singlet emission is excluded from the emission spectrum, and the triplet emission spectrum is analyzed to confirm its presence. When electrons are excited by the light source, the two components can be separated at extremely low temperatures because electrons spend a much longer time in the triplet state than in the singlet state.

[0191] According to one embodiment of this specification, the triplet energy (E) T1The phosphorescence intensity can be calculated using the method described below. After cooling the sample to 77K, irradiate the sample with excitation light (360nm). After measuring the phosphorescence intensity using a streak camera, draw a tangent line at the rising point of the phosphorescence spectrum and determine the wavelength value λ[nm] at the intersection of this tangent line and the x-axis. Substitute this wavelength value into Equation 1 below to calculate the energy value E. T1 The emission spectrum was then measured using a nitrogen molecular laser (MNL200, manufactured by Lasertechnik Berlin) and a streak camera (C4334, manufactured by Hamamatsu Photonics Co., Ltd.).

[0192] [Formula 1]

[0193] E T1 [eV] = 1239.85 / λ edge

[0194] In one embodiment of this specification, the triplet energy level (T1) can be calculated using Gaussian 03, a quantum chemistry calculation program manufactured by Gaussian Corporation. Specifically, using density functional theory (DFT), with B3LYP (Becke, a three-parameter Lee-Yang-Parr function) as the functional and 6-31G* as the basis functions, the calculated value of the triplet energy can be obtained by time-dependent density functional theory (TD-DFT) for the optimized structure.

[0195] In one embodiment of this specification, the maximum emission peak of the light-emitting layer is located in the range of 400 nm to 500 nm. That is, the light-emitting layer containing the compound of chemical formula 1 and the compound of chemical formula 2 emits blue light.

[0196] In one embodiment of this specification, the weight ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 is 1:99 to 50:50. Preferably, it is 5:95 to 40:60. More preferably, it is 10:90 to 30:70. When the above range is satisfied, the low voltage and high efficiency of the anthracene-based host are reproduced, and electron injection into the triplet energy level of the dopant becomes easier, increasing the exciton formation ratio, thus having the advantage of improved luminescence efficiency.

[0197] In one embodiment of this specification, the light-emitting layer can be formed by co-evaporation of a compound of chemical formula 1 and a compound of chemical formula 2.

[0198] The compounds of chemical formula 2 will now be described in detail.

[0199] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0200] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heterocyclic group.

[0201] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0202] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0203] In one embodiment of this specification, Ar11 and Ar12 are heterocyclic groups containing O or S as heteroelements.

[0204] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each independently may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted naphthobenzothiophenyl.

[0205] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, each being independently a C6-C30 aryl group substituted with or unsubstituted with deuterium; or a C2-C30 heterocyclic group substituted with or unsubstituted with deuterium, a C6-C30 aryl group, or a C6-C30 aryl group substituted with deuterium.

[0206] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, each being independently a C6-C20 aryl group substituted with or unsubstituted with deuterium; or a C2-C20 heterocyclic group substituted with or unsubstituted with deuterium, a C6-C20 aryl group, or a C6-C20 aryl group substituted with deuterium.

[0207] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each may independently be a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted terphenyl; a deuterated or unsubstituted naphthyl; a deuterated or unsubstituted phenanthryl; a dibenzofuranyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; a dibenzothiophenyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; a naphthobenzofuranyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; or a naphthobenzothiophenyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group.

[0208] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each may independently be a deuterated or unsubstituted phenyl; a deuterated or unsubstituted 1-naphthyl; a deuterated or unsubstituted 2-naphthyl; a deuterated or unsubstituted 9-phenanthyl; a deuterated, phenyl, or phenyl-d5-substituted or unsubstituted 1-dibenzofuranyl; a deuterated, phenyl, or phenyl-d5-substituted or unsubstituted 2-dibenzofuranyl; a deuterated, phenyl, or phenyl-d5-substituted or unsubstituted 3-dibenzofuranyl; and a deuterated, phenyl, or phenyl-d5-substituted or unsubstituted 4-dibenzofuranyl.

[0209] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each independently represents phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, or naphthobenzothiophenyl.

[0210] In one embodiment of this specification, Ar11 and Ar12 may be the same as or different from each other, and each is independently phenyl, naphthyl, dibenzofuranyl, or naphthobenzofuranyl.

[0211] In one embodiment of this specification, either Ar11 or Ar12 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heterocyclic group.

[0212] In one embodiment of this specification, Ar11 is a substituted or unsubstituted aryl group, and Ar12 is a substituted or unsubstituted heterocyclic group.

[0213] In one embodiment of this specification, Ar11 is a substituted or unsubstituted heterocyclic group, and Ar12 is a substituted or unsubstituted aryl group.

[0214] In one embodiment of this specification, Ar13 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0215] In one embodiment of this specification, Ar13 is hydrogen, deuterium, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.

[0216] In one embodiment of this specification, Ar13 is hydrogen, deuterium, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0217] In one embodiment of this specification, Ar13 is hydrogen; deuterium; a C6-C30 aryl group substituted or unsubstituted with deuterium; or a C2-C30 heterocyclic group substituted or unsubstituted with deuterium, a C6-C30 aryl group, or a C6-C30 aryl group substituted or unsubstituted with deuterium.

[0218] In one embodiment of this specification, Ar13 is hydrogen; deuterium; a C6-C20 aryl group substituted or unsubstituted with deuterium; or a C2-C20 heterocyclic group substituted or unsubstituted with deuterium, a C6-C20 aryl group, or a C6-C20 aryl group substituted or unsubstituted with deuterium.

[0219] In one embodiment of this specification, Ar13 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthryl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group; a dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group; or a naphthobenzothiophenyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group.

[0220] In one embodiment of this specification, Ar13 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a 1-naphthyl group substituted or unsubstituted with deuterium; a 2-naphthyl group substituted or unsubstituted with deuterium; a 9-phenanthyl group substituted or unsubstituted with deuterium; a 1-dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5yl; a 2-dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5yl; a 3-dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5yl; and a 4-dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5yl.

[0221] In one embodiment of this specification, Ar13 is hydrogen or deuterium.

[0222] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0223] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C60 aryl group.

[0224] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C30 aryl group.

[0225] In one embodiment of this specification, L11 and L12 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, or substituted or unsubstituted naphthylene.

[0226] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a C6-C30 aryl group that is directly bonded, or substituted with deuterium, or unsubstituted.

[0227] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a C6-C20 aryl group that is directly bonded, or substituted with deuterium, or unsubstituted.

[0228] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenylene, or a deuterated or unsubstituted naphthylene.

[0229] In one embodiment of this specification, L11 is a direct bond.

[0230] In one embodiment of this specification, L12 is a direct bond.

[0231] In one embodiment of this specification, L11 and L12 may be the same as or different from each other, and each may be directly bonded or selected from any of the following structures.

[0232]

[0233] In the above structure, D refers to deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

[0234] In one embodiment of this specification, k1 is 1 or more. In another embodiment, k1 is 2 or more. In another embodiment, k1 is 3 or more. In another embodiment, k1 is 4.

[0235] In one embodiment of this specification, k2 is 1 or more. In another embodiment, k2 is 2 or more. In another embodiment, k2 is 3 or more. In another embodiment, k2 is 4 or more. In another embodiment, k2 is 5 or more. In another embodiment, k2 is 6.

[0236] In one embodiment of this specification, m1 is 1 or more. In another embodiment, m1 is 2 or more. In another embodiment, m1 is 3 or more. In another embodiment, m1 is 4 or more. In another embodiment, m1 is 5 or more. In another embodiment, m1 is 6 or more. In another embodiment, m1 is 7 or more. In another embodiment, m1 is 8 or more.

[0237] In one embodiment of this specification, the above-mentioned chemical formula 2 is selected from one of the following compounds.

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] The compound according to one embodiment of this specification can be manufactured by the manufacturing method described later. Substituents can be added or removed as needed, and the positions of the substituents can be changed. Furthermore, based on techniques known in the art, the starting material, reactants, reaction conditions, etc., can be modified. The manufacturing method can be further specified through manufacturing examples described later, and the reaction sequence can be changed depending on the compound. The method for synthesizing the anthracene compound of chemical formula 1 described above is not limited to the method described above.

[0244] This specification provides organic light-emitting devices containing the compounds described above.

[0245] 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.

[0246] In this specification, when a part is indicated to "include" a certain component, unless otherwise stated, it means that other components may be included, rather than excluded.

[0247] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0248] In this specification, the meaning of "a specific substance A is contained in layer B" includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0249] In this specification, the term "a specific substance A is contained in layer C or layer D" means all of the following: i) contained in one or more layers of layer C, or ii) contained in one or more layers of layer D, or iii) contained in one or more layers of layer C and one or more layers of layer D, respectively.

[0250] The organic layer 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, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited to this.

[0251] In one embodiment of this specification, the light-emitting layer may be formed of a single-layer structure, or it may include two or more light-emitting layers. When the light-emitting layer is a single layer, it contains both the compound of chemical formula 1 and the compound of chemical formula 2 in one layer. When the light-emitting layer includes two or more light-emitting layers, one layer may contain both the compound of chemical formula 1 and the compound of chemical formula 2, or different light-emitting layers may each contain the compound of chemical formula 1 and the compound of chemical formula 2. For example, the light-emitting layer may include a first light-emitting layer containing the compound of chemical formula 1 and a second light-emitting layer containing the compound of chemical formula 2. In this case, the second light-emitting layer may be disposed between the first light-emitting layer and the cathode. The first light-emitting layer and the second light-emitting layer may be disposed in contact with each other. When the first light-emitting layer and the second light-emitting layer each contain the compound of chemical formula 1 and the compound of light-emitting layer 2 as the main components, the first light-emitting layer and the second light-emitting layer may also each contain a dopant compound. At this point, the first light-emitting layer and the aforementioned second light-emitting layer may contain dopant materials of the same type or different types, but it is preferable that they contain dopant materials of the same type.

[0252] In one embodiment of this specification, the light-emitting layer comprises the compound of chemical formula 1 and the compound of chemical formula 2 as the main body.

[0253] In one embodiment of this specification, the light-emitting layer further comprises a dopant material. The dopant is a phosphorescent dopant or a fluorescent dopant; as a fluorescent dopant, it may comprise an arylamine compound or a boron-containing polycyclic compound.

[0254] In one embodiment of this specification, the light-emitting layer further comprises a dopant material, which is an arylamine compound or a boron-containing polycyclic compound.

[0255] In one embodiment of this specification, the dopant is a compound represented by any one of the following chemical formulas Z1 to Z3. Specifically, the arylamine compound is a compound of chemical formula Z1 or Z2, and the boron-containing polycyclic compound is a compound of chemical formula Z3.

[0256] [Chemical Formula Z1]

[0257]

[0258] [Chemical formula Z2]

[0259]

[0260] [Chemical formula Z3]

[0261]

[0262] In the above chemical formulas Z1 to Z3,

[0263] X3 and X4 are either hydrogen or deuterium, or they may be directly bonded together to form a ring.

[0264] R41 and R42 may be the same as or different from each other, and each may be independently hydrogen, deuterium, or substituted or unsubstituted alkyl groups.

[0265] Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0266] Cy1 to Cy3 may be the same as or different from each other, and each can be an aromatic hydrocarbon ring consisting of a single ring or multiple rings, or an aromatic heterocycle consisting of a single ring or multiple rings.

[0267] R31, R32, R43 to R46, and R51 to R53 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combination with adjacent substituents.

[0268] r41, r42, and r51 to r53 are each integers from 0 to 4. When they are 2 or more, the substituents in the parentheses are the same or different from each other.

[0269] In one embodiment of this specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and each is independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0270] In one embodiment of this specification, Ar31 to Ar34, Ar41 to Ar44, Ar51, and Ar52 may be the same as or different from each other, and each is independently a C6-C20 aryl group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C6 alkyl groups, or by substituents selected from two or more groups connected in the above group; or a C2-C20 heterocyclic group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C6 alkyl groups, or by substituents selected from two or more groups connected in the above group.

[0271] In one embodiment of this specification, Cy1 to Cy3 may be the same as or different from each other, each being an aromatic hydrocarbon ring consisting of a monocyclic to a 3-ring ring; or an aromatic heterocycle consisting of a monocyclic to a 3-ring ring containing N, O or S.

[0272] In one embodiment of this specification, Cy1 to Cy3 may be the same as or different from each other, and each is independently a benzene ring, a naphthalene ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, or a dibenzothiophene ring, and may be further fused with C5-C10 aliphatic hydrocarbon rings.

[0273] In one embodiment of this specification, R31, R32, R43 to R46, and R51 to R53 may be the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C90 arylsilyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C2-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, or a C3-C30 hydrocarbon ring or a substituted or unsubstituted C2-C30 heterocyclic ring formed by combining with adjacent substituents.

[0274] In one embodiment of this specification, the dopant is a compound with the chemical formula Z3.

[0275] In one embodiment of this specification, the above chemical formula Z3 is any one of the following chemical formulas Z3-1 to Z3-3.

[0276] [Chemical Formula Z3-1]

[0277]

[0278] [Chemical Formula Z3-2]

[0279]

[0280] [Chemical Formula Z3-3]

[0281]

[0282] In the above chemical formulas Z3-1 to Z3-3,

[0283] R51 to R53, r52, Ar51, and Ar52 are defined in the same way as in chemical formula Z3.

[0284] X5 is 0 or S.

[0285] r521 is an integer from 0 to 2. When r521 is 2, R52 is either the same or different from each other.

[0286] In one embodiment of this specification, Ar51 and Ar52 may be the same as or different from each other, and each is independently a C6-C30 aryl group or a C2-C30 heterocyclic group with or without an aliphatic hydrocarbon ring. The aryl or heterocyclic group is substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C10 alkyl groups, or by two or more substituents selected from the group above.

[0287] In one embodiment of this specification, the aryl or heterocyclic group of Ar51 contains a substituent that is not hydrogen at the position of the N-ortho orientation of the connection.

[0288] In one embodiment of this specification, the aryl or heterocyclic group of Ar52 contains a substituent that is not hydrogen at the position of the N-ortho orientation of the connection.

[0289] In one embodiment of this specification, R51 to R53 may be the same as or different from each other, and each independently represents hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C90 arylsilyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C2-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic, or combined with adjacent substituents to form a C3-C30 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

[0290] In one embodiment of this specification, R51 to R53 may be the same as or different from each other, and each independently is hydrogen, deuterium, methyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, diphenylamino or bis((tert-butyl)phenyl)amino.

[0291] In one embodiment of this specification, two adjacent R51s, two adjacent R52s, or two adjacent R53s combine with each other to form a substituted or unsubstituted ring. In this case, the ring is a C3-C30 aliphatic hydrocarbon ring or a C6-C30 aromatic hydrocarbon ring; specifically, it is a cyclopentene, cyclohexene, tetrahydronaphthalene ring, benzene ring, or naphthalene ring.

[0292] In one embodiment of this specification, the dopant may be selected from the structures described below, but is not limited thereto.

[0293]

[0294] In one embodiment of this specification, the dopant in the light-emitting layer may contain 0.01 parts by weight to 50 parts by weight, preferably 0.1 parts by weight to 30 parts by weight, and more preferably 1 part by weight to 10 parts by weight, based on 100 parts by weight of the main body. Within the above range, energy transfer from the main body to the dopant is effectively formed. In this case, 100 parts by weight of the main body is based on the total weight of the compound of Chemical Formula 1 and the compound of Chemical Formula 2.

[0295] In one embodiment of this specification, the organic layer includes two or more light-emitting layers, one of which contains a compound of chemical formula 1.

[0296] In one embodiment of this specification, the maximum emission peaks of the two or more light-emitting layers are different from each other. The light-emitting layer containing the compound of Formula 1 is blue, and the light-emitting layer not containing the compound of Formula 1 may contain blue, red, or green light-emitting compounds known in the art.

[0297] In one embodiment of this specification, the light-emitting layer containing the compound of chemical formula 1 and the compound of chemical formula 2 contains a fluorescent dopant, and the light-emitting layer not containing the compound of chemical formula 1 and the compound of chemical formula 2 contains a phosphorescent dopant.

[0298] According to one embodiment of this specification, the organic layer of the organic light-emitting device includes two or more light-emitting layers. The maximum emission peak of one light-emitting layer (light-emitting layer 1) is 400 nm to 500 nm, and the maximum emission peak of the other light-emitting layer (light-emitting layer 2) can be 510 nm to 580 nm or 610 nm to 680 nm. In this case, light-emitting layer 1 contains the compound of chemical formula 1 and the compound of chemical formula 2.

[0299] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0300] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0301] The organic light-emitting device structure described in this specification can have the following characteristics: Figure 1 and 2 The structure shown is not limited to this.

[0302] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a substrate 101, an anode 102, a light-emitting layer 106, and a cathode 110 are sequentially stacked. In the structure shown above, the compounds of Chemical Formula 1 and Chemical Formula 2 may be included in the light-emitting layer 106.

[0303] Figure 2 The diagram illustrates the structure of an organic light-emitting device comprising a substrate 101, an anode 102, a hole injection layer 103, a first hole transport layer 104, a second hole transport layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, and a cathode 110, stacked sequentially. In the structure shown above,

[0304] The organic light-emitting devices described in this specification, except that the organic layer contains the aforementioned compounds, can be manufactured using materials and methods known in the art.

[0305] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0306] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form the anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as the cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0307] In addition to vacuum evaporation, organic layers can also be formed using solution coating methods when manufacturing organic light-emitting devices. Here, solution coating methods refer to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but are not limited to these.

[0308] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to these methods.

[0309] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, 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 not limited to these.

[0310] As the cathode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0311] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include dibenzofuran derivatives and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0312] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., which have aryl amine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. Furthermore, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0313] The aforementioned hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Furthermore, it is preferably a material with excellent thin film forming ability. Furthermore, 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, 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, polyaniline, polythiophene-based conductive polymers, etc.

[0314] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. It can be a single layer or a multilayer structure with two or more layers. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, preferably a substance with high hole mobility. Specific examples include arylamine-based organic compounds, carbazole-based compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0315] In one embodiment of this specification, the hole transport layer is a multilayer structure with two or more layers. Specifically, it is a two-layer structure, and each layer contains a different material.

[0316] The aforementioned electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a material with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavonoid-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are typically materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are examples, each accompanied by an aluminum or silver layer.

[0317] The aforementioned electron injection layer is a layer that receives electrons from the electrode. The electron injection material preferably has excellent electron transport capabilities, effectively receiving electrons from the second electrode, and exhibits excellent electron injection performance for the light-emitting layer or light-emitting material. Furthermore, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film formation capabilities. Specifically, materials such as fluorenone, anthraquinone dimethane, biphenylquinone, and thiamethoxam dioxide are preferred. 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.

[0318] 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.

[0319] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, thereby improving the device's lifetime and efficiency. Known materials can be used without restriction and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0320] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. Specifically, there are... Diazole derivatives or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0321] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0322] Hereinafter, in order to provide a detailed description of this specification, embodiments and comparative examples will be given. However, various modifications can be made based on the embodiments and comparative examples described herein, and this should not be construed as limiting the scope of this specification to the embodiments and comparative examples detailed below. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0323] [Manufacturing of Chemical Formulas 1 and 2]

[0324]

[0325] (Manufacturing Example 1) Manufacturing of Compound BH1-1

[0326] (Manufacturing Example 1-1) Manufacturing of Compound BH1-1-1

[0327] In a three-necked flask, phenanthrene-9-ylboronic acid (50.0 g, 225 mmol) and 2-bromo-6-chloronaphthalene (59.8 g, 248 mmol) were dissolved in 500 ml of 1,4-dichloronaphthalene solution. In an alkane, K₂CO₃ (62.1 g, 450 mmol) was dissolved in 200 mL of H₂O and added. Pd(P(t-Bu)₃)₂ (1.14 g, 2.3 mmol) was then added, and the mixture was stirred for 5 hours under reflux at an argon atmosphere. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, concentrated, and purified by silica gel column chromatography to obtain 49.9 g of compound BH₁-1-1. (Yield 65%, MS [M+H]) + =339)

[0328] (Manufacturing Examples 1-2) Manufacturing of Compound BH1-1

[0329] In a three-necked flask, BH1-1-1 (20 g, 58.9 mmol) and dibenzo[b,d]furan-2-ylboronic acid (13.7 g, 64.8 mmol) were dissolved in 200 ml of 1,4-dioxane. In an alkane, K₃CO₄ (25.0 g, 117.8 mmol) was dissolved in 70 mL of H₂O and added. Pd(P(t-Bu)₃)₂ (0.30 g, 0.59 mmol) was then added, and the mixture was stirred for 5 hours under reflux at an argon atmosphere. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, concentrated, and purified by silica gel column chromatography to obtain 12.2 g of compound BH₁-1. (Yield 44%, MS [M+H)) + =471)

[0330]

[0331] (Manufacturing Example 2) Manufacturing of Compound BH1-2

[0332] (Manufacturing Example 2-1) Manufacturing of Compound BH1-2-1

[0333] Using 1-bromo-4-chlorobenzene instead of 2-bromo-6-chloronaphthalene, 48.1 g of compound BH1-2-1 was obtained by the same method as in Preparation Example 1-1. (Yield 74%, MS [M+H]) + =289)

[0334] (Manufacturing Example 2-2) Manufacturing of Compound BH1-2

[0335] Compound BH1-2 was obtained by the same method as in Examples 1-2, except that compound BH1-2-1 was used instead of compound BH1-1-1, and naphtho[2,3-b]benzofuran-3-ylboronic acid was used instead of dibenzo[b,d]furan-2-ylboronic acid. (Yield 41%, MS[M+H)) + =471)

[0336]

[0337] (Manufacturing Example 3) Manufacturing of Compound BH1-3

[0338] (Manufacturing Example 3-1) Manufacturing of Compound BH1-3-1

[0339] Using pyrene-1-ylboronic acid instead of phenanthrene-9-ylboronic acid, 45.0 g of compound BH1-3-1 was obtained by the same method as in Preparation Example 1-1. (Yield 62%, MS [M+H]) + =365)

[0340] (Manufacturing Example 3-2) Manufacturing of Compound BH1-3

[0341] Compound BH1-3 was obtained by using compound BH1-3-1 instead of compound BH1-1-1, and dibenzo[b,d]furan-4-ylboronic acid instead of dibenzo[b,d]furan-2-ylboronic acid, except that 10.9 g of compound BH1-3 was obtained by the same method as in Examples 1-2. (Yield 40%, MS[M+H)) + =497)

[0342]

[0343] (Manufacturing Example 4) Manufacturing of Compound BH1-4

[0344] (Manufacturing Example 4-1) Manufacturing of Compound BH1-4-1

[0345] Using 1-bromo-4-chlorobenzene instead of 2-bromo-6-chloronaphthalene, 43.6 g of compound BH1-4-1 was obtained by the same method as in Preparation Example 3-1. (Yield 69%, MS [M+H]) + =315)

[0346] (Manufacturing Example 4-2) Manufacturing of Compound BH1-4

[0347] Compound BH1-4 was obtained by using compound 1-4-1 instead of compound 1-3-1, and (7-phenyldibenzo[b,d]furan-2-yl)boronic acid instead of dibenzo[b,d]furan-2-ylboronic acid, except that 12.8 g of compound BH1-4 was obtained by the same method as in Example 3-2. (Yield 39%, MS[M+H)) + =523)

[0348]

[0349] (Manufacturing Example 5) Manufacturing of Compound BH1-5

[0350] (Manufacturing Example 5-1) Manufacturing of Compound BH1-5-1

[0351] Compound BH1-5-1 was obtained in 44.7 g by the same method as in Example 1-1, except that triphenylen-2-ylboronic acid was used instead of phenanthrene-9-ylboronic acid and 2-bromo-8-chlorodibenzo[b,d]furan was used instead of 2-bromo-6-chloronaphthalene. (Yield 57%, MS [M+H]) + =429)

[0352] (Manufacturing Example 5-2) Manufacturing of Compound BH1-5

[0353] Compound BH1-5 was obtained in 13.8 g by the same method as in Examples 1-2, except that compound BH1-5-1 was used instead of compound BH1-1-1, and naphthalene-2-ylboronic acid was used instead of dibenzo[b,d]furan-2-ylboronic acid. (Yield 57%, MS [M+H]) + =521)

[0354]

[0355] (Manufacturing Example 6) Manufacturing of Compound BH1-6

[0356] (Manufacturing Example 6-1) Manufacturing of Compound BH1-6-1

[0357] Using 2-phenylene-2-ylboronic acid instead of phenanthrene-9-ylboronic acid, 51.0 g of compound BH1-6-1 was obtained by the same method as in Preparation Example 1-1. (Yield 71%, MS [M+H]) + =389)

[0358] (Manufacturing Example 6-2) Manufacturing of Compound BH1-6

[0359] Compound BH1-6-1 was used instead of compound BH1-1-1, and 10.5 g of compound BH1-6 was obtained by the same method as in Manufacturing Examples 1-2. (Yield 39%, MS [M+H]) + =521)

[0360]

[0361] (Manufacturing Example 7) Manufacturing of Compound BH1-7

[0362] (Manufacturing Example 7-1) Manufacturing of Compound BH1-7-1

[0363] Using fluoranthen-3-ylboronic acid instead of phenanthrene-9-ylboronic acid, 41.2 g of compound BH1-7-1 was obtained by the same method as in Preparation Example 2-1. (Yield 65%, MS [M+H]) + =204)

[0364] (Manufacturing Example 7-2) Manufacturing of Compound BH1-7

[0365] Compound BH1-7 was obtained in the same manner as in Manufacturing Example 1-2, except that compound 1-7-1 was used instead of compound 1-1-1. (Yield 46%, MS [M+H]) + =445)

[0366]

[0367] (Manufacturing Example 8) Manufacturing of Compound BH1-8

[0368] Using naphtho[2,3-b]benzofuran-4-ylboronic acid instead of dibenzo[b,d]furan-2-ylboronic acid, 12.2 g of compound BH1-8 was obtained by the same method as in Preparation Example 7-2. (Yield 39%, MS[M+H)) + =495)

[0369]

[0370] (Manufacturing Example 9) Manufacturing of Compound BH2-1

[0371] (Manufacturing Example 9-1) Manufacturing of Compound BH2-1-1

[0372] In a three-necked flask, 9-bromoanthracene (50.0 g, 194 mmol) and naphthalene-1-boronic acid (36.79 g, 214 mmol) were dissolved in 500 ml of 1,4-dioxane. In an alkane, K₂CO₃ (80.6 g, 583 mmol) was dissolved in 200 mL of H₂O and added. Pd(P(t-Bu)₃)₂ (1.98 g, 3.9 mmol) was then added, and the mixture was stirred for 5 hours under reflux at an argon atmosphere. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, concentrated, and purified by silica gel column chromatography to obtain 49.8 g of compound BH₂-1-1. (Yield 84%, MS [M+H]) + =305)

[0373] (Manufacturing Example 9-2) Manufacturing of Compound BH2-1-2

[0374] In a two-necked flask, compound BH2-1-1 (20.0 g, 65.7 mmol), N-bromosuccinimide (NBS) (11.8 g, 65.7 mmol), and 300 mL of dimethylformamide (DMF) were added. The mixture was stirred at room temperature under an argon atmosphere for 10 hours. After the reaction was complete, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO4, filtered, concentrated, and then purified by silica gel column chromatography to obtain 18.5 g of compound BH2-1-2. (Yield 74%, MS [M+H]) + =383)

[0375] (Manufacturing Example 9-3) Manufacturing of Compound BH2-1

[0376] In a three-necked flask, compound BH2-1-2 (20.0 g, 52.2 mmol) and naphthalene-2-boronic acid (9.9 g, 57.4 mmol) were dissolved in 300 ml of 1,4-di(2 ... In an alkane, K₂CO₃ (14.4 g, 10⁴ mmol) was dissolved in 100 mL of H₂O and added. Pd(P(t-Bu)₃)₂ (0.27 g, 0.52 mmol) was then added, and the mixture was stirred for 5 hours under reflux at an argon atmosphere. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, concentrated, and purified by silica gel column chromatography to obtain 11.9 g of compound BH₂-1. (Yield 52%, MS [M+H]) + =431)

[0377]

[0378] (Manufacturing Example 10) Manufacturing of Compound BH2-2

[0379] Using naphtho[2,1-b]benzofuran-10-ylboronic acid instead of naphthalene-2-boronic acid, 10.1 g of compound BH2-2 was obtained by the same method as in Preparation Example 9-3. (Yield 37%, MS[M+H)) + =521)

[0380]

[0381] (Manufacturing Example 11) Manufacturing of Compound BH2-3

[0382] (Manufacturing Example 11-1) Manufacturing of Compound BH2-3-1

[0383] 40.3 g of compound BH2-3-1 was obtained by the same method as in Preparation Example 9-1. (Yield 81%, MS [M+H]) + =255)

[0384] (Manufacturing Example 11-2) Manufacturing of Compound BH2-3-2

[0385] 18.8 g of compound BH2-3-2 was obtained by the same method as in Preparation Example 9-2. (Yield 72%, MS [M+H]) + =334)

[0386] (Manufacturing Example 11-3) Manufacturing of Compound BH2-3

[0387] 11.7 g of compound BH2-3 was obtained by the same method as in Preparation Example 9-3. (Yield 46%, MS [M+H]) + =421)

[0388] [Experimental Example 1] Fabrication of Organic Light-Emitting Devices

[0389] Example 1

[0390] A glass substrate coated with an ITO (Indium Tin Oxide) film at a thickness of 150 nm was immersed in distilled water containing detergent and ultrasonically washed. 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 ultrasonic washing was repeated twice with distilled water for 10 minutes each time. 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 nitrogen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0391] On the prepared ITO transparent electrode, a hole injection layer is formed by thermal vacuum evaporation of the following HAT-CN compound to a thickness of 5 nm. Next, a first hole transport layer is formed by thermal vacuum evaporation of HTL1 to a thickness of 100 nm, followed by a second hole transport layer formed by thermal vacuum evaporation of HTL2 to a thickness of 10 nm. Then, a 20 nm thick light-emitting layer is formed by co-evaporation of BD (2 wt% of the total 100 wt% of the light-emitting layer) as a dopant and compounds BH1-1 and BH2-1 (weight ratio 20:80, totaling 98 wt% of the total 100 wt% of the light-emitting layer) as the main components. Next, an electron transport layer is formed by vacuum evaporation of ETL to a thickness of 20 nm. Then, an electron injection layer is formed by vacuum evaporation of LiF to a thickness of 0.5 nm. Finally, a cathode is formed by evaporation of aluminum to a thickness of 100 nm, thereby fabricating an organic light-emitting device.

[0392]

[0393] During the above process, the evaporation rate of the organic material was maintained at 0.04 nm / s to 0.09 nm / s, the lithium fluoride of the electron injection layer was maintained at 0.03 nm / s, and the aluminum of the cathode was maintained at 0.2 nm / s. During evaporation, the vacuum level was maintained at 1×10⁻⁶. -7 Up to 5X10 -5 This led to the creation of organic light-emitting devices.

[0394] Examples 2 to 22 and Comparative Examples 1 to 7

[0395] In Example 1 above, the compounds listed in Table 1 below were used as the host compounds for the light-emitting layer. Otherwise, the organic light-emitting device was manufactured using the same method as in Example 1 above. Specifically, Examples 1 to 22 used a mixture of two host compounds, while Comparative Examples 1 to 7 used only one host compound.

[0396]

[0397] For the organic light-emitting devices manufactured in Examples 1 to 22 and Comparative Examples 1 to 7 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T97) at the given current density was measured relative to 97% of the initial brightness. The results are shown in Table 2 below.

[0398] [Table 1]

[0399]

[0400]

[0401] [Table 2]

[0402]

[0403]

[0404] It can be seen that Examples 1 to 22 in Table 1 above contain compounds of both Chemical Formula 1 and Chemical Formula 2, thereby enhancing the low voltage, high efficiency and long lifespan characteristics of the device.

[0405] Compared with Comparative Examples 1 to 3, which contain only compounds of Formula 2, Examples 1 to 22 of the present invention exhibit a voltage reduction of up to 10.6%, an efficiency increase of up to 8.75%, and a lifetime increase of up to 76.25%. Compared with Comparative Examples 4 to 8, which contain only compounds of Formula 1, Examples 1 to 22 of the present invention exhibit a voltage reduction of up to 32.8%, an efficiency increase of up to 58.2%, and a lifetime increase of up to 370%.

[0406] [Experimental Example 2] Determination of triplet energy of compound with chemical formula 1

[0407] The emission spectrum was measured using a nitrogen molecular laser (MNL200, manufactured by Edby Photonics) and a streak camera (C4334, manufactured by Hamamatsu Photonics).

[0408] Triple state energy (E) T1 The phosphorescence intensity can be calculated as follows: After cooling the sample to 77K, the sample for phosphorescence measurement is irradiated with excitation light (360nm), and the phosphorescence intensity is measured using a streak camera. Then, a tangent is drawn to the rising point of the phosphorescence spectrum, and the wavelength value λ [nm] at the intersection of this tangent and the x-axis is determined. This wavelength value is substituted into Equation 1 below to calculate the energy value E. T1 The values ​​are recorded in Table 3 below.

[0409] [Formula 1]

[0410] E T1 [eV] = 1239.85 / λ edge

[0411] [Table 3]

[0412] compound <![CDATA[Triplet energy E T1 (eV)]]> BH 1-1 2.54 BH 1-2 2.57 BH 1-3 2.11 BH 1-4 2.08 BH 1-5 2.24 BH 1-6 2.21 BH 1-7 2.30 BH 1-8 2.33 BH 2-1 1.67 BH 2-2 1.69 BH 2-3 1.70

[0413] Observing Table 3 above, it can be seen that the triplet energy of the compound of Formula 1 of the present invention is above 2 eV, and is higher than that of the compound of Formula 2. It can be confirmed that the compound of Formula 1 utilizes a higher triplet energy level, and through electron migration to the triplet energy level of the dopant, additional efficiency is increased.

[0414] Example 23

[0415] A glass substrate with an ITO (indium tin oxide) film coated to a thickness of 150 nm was immersed in distilled water containing detergent and ultrasonically cleaned. The detergent used was from Fischer, and the distilled water was filtered twice using a Millipore filter. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After distilled water cleaning, the substrate was ultrasonically cleaned with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Furthermore, the substrate was cleaned with nitrogen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0416] On the prepared ITO transparent electrode, a hole injection layer was formed by thermal vacuum evaporation of the following HAT-CN compound to a thickness of 5 nm. Next, a first hole transport layer was formed by thermal vacuum evaporation of HTL1 to a thickness of 100 nm, followed by a second hole transport layer formed by thermal vacuum evaporation of HTL2 to a thickness of 10 nm. Then, a first light-emitting layer with a thickness of 5 nm was formed by co-evaporation of BD (2% by weight relative to 100% of the total light-emitting layer weight) as a dopant and compound BH1-1 as the host. Next, a second light-emitting layer with a thickness of 20 nm was deposited on the first light-emitting layer by co-evaporation of BD (2% by weight relative to 100% of the total light-emitting layer weight) as a dopant and compound BH2-1 as the host. Next, an electron transport layer was formed by vacuum evaporation of ETL to a thickness of 20 nm. Finally, an electron injection layer was formed by vacuum evaporation of LiF to a thickness of 0.5 nm. Next, aluminum is vapor-deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light-emitting device.

[0417]

[0418] During the above process, the evaporation rate of the organic material was maintained at 0.04 nm / s to 0.09 nm / s, the lithium fluoride of the electron injection layer was maintained at 0.03 nm / s, and the aluminum of the cathode was maintained at 0.2 nm / s. During evaporation, the vacuum level was maintained at 1×10⁻⁶. -7 Up to 5X10 -5 This led to the creation of organic light-emitting devices.

[0419] Examples 24 to 39 and Comparative Examples 10 to 14

[0420] In Example 23 described above, the compounds listed in Table 4 below were used as the host compounds for the light-emitting layer, and the device was otherwise manufactured using the same method as in Example 23. Comparative Examples 10 to 14 used only one layer of light-emitting layer.

[0421]

[0422] For the organic light-emitting devices manufactured in Examples 23 to 39 and Comparative Examples 1 to 7 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T97) at the current density was measured relative to 97% of the initial brightness. The results are shown in Table 5 below.

[0423] [Table 4]

[0424] First light-emitting layer Second light-emitting layer Example 23 BH 1-1 BH 2-1 Example 24 BH 1-1 BH 2-2 Example 25 BH 1-2 BH 2-1 Example 26 BH 1-2 BH 2-2 Example 27 BH 1-2 BH 2-3 Example 28 BH 1-4 BH 2-1 Example 29 BH 1-4 BH 2-2 Example 30 BH 1-4 BH 2-3 Example 31 BH 1-5 BH 2-1 Example 32 BH 1-5 BH 2-2 Example 33 BH 1-5 BH 2-3 Example 34 BH 1-6 BH 2-1 Example 35 BH 1-6 BH 2-3 Example 36 BH l-7 BH 2-1 Example 37 BH 1-7 BH 2-2 Example 38 BH 1-8 BH 2-1 Example 39 BH 1-8 BH 2-2 Comparative Example 9 BH 1-1 Comparative Example 10 BH 1-3 Comparative Example 11 BH 1-5 Comparative Example 12 BH 2-1 Comparative Example 13 BH 2-2 Comparative Example 14 BH 2-3

[0425] Table 5]

[0426]

[0427] It can be seen that when a device is fabricated with two light-emitting layers, it exhibits the characteristics of low voltage, high efficiency and long lifespan, similar to the case of using a single light-emitting layer formed by co-evaporation.

[0428] [Symbol Explanation]

[0429] 101: Substrate

[0430] 102: Anode

[0431] 103: Hole Injection Layer

[0432] 104: First Hole Transport Layer

[0433] 105: Second Hole Transport Layer

[0434] 106: Emissive layer

[0435] 107: Electron Transport Layer

[0436] 108: Electron Injection Layer

[0437] 110: Cathode.

Claims

1. An organic light-emitting device, wherein, include: Anode, cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer. The maximum emission peak of the light-emitting layer exists in the range of 400 nm to 500 nm. The light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 2: Chemical Formula 1 In the chemical formula 1, Ar1 is a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthyl group. L1 is a directly bonded, substituted, or unsubstituted aryl group. X1 is either O or S. One of R1 to R8 is attached to L1, and the others may be the same as or different from each other. Each of them is independently hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, or combined with adjacent substituents to form a substituted or unsubstituted ring. n1 is an integer from 0 to 3. Chemical formula 2 In the chemical formula 2, D stands for deuterium. Ar11 and Ar12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Ar13 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. L11 and L12 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group. m1 is an integer from 0 to 7.

2. The organic light-emitting device according to claim 1, wherein, The triplet energy level T1 of the compound of chemical formula 1 is higher than that of the compound of chemical formula 2.

3. The organic light-emitting device according to claim 1, wherein, The triplet energy level T1 of the compound of chemical formula 1 is above 2.0 eV.

4. The organic light-emitting device according to claim 1, wherein, The Ar1 is any one of the following chemical formulas: PAr1, PAr2, and PAr4: Chemical formula PAr1 Chemical formula PAr2 Chemical formula PAr4 Among PAr1, PAr2 and PAr4, The dashed line represents the portion connected to L1 of chemical formula 1. G1 to G3, G6 and G7 may be the same as or different from each other, and each is independently a hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. g1 and g7 are integers from 0 to 3, g2 is an integer from 0 to 8, g3 is an integer from 0 to 9, and g6 is an integer from 0 to 6. When g1 to g3, g6 and g7 are each 2 or more, the substituents in the parentheses may be the same or different from each other.

5. An organic light-emitting device, wherein, include: Anode, cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer. The maximum emission peak of the light-emitting layer exists in the range of 400 nm to 500 nm. The luminescent layer comprises a compound of any one of the following chemical formulas 101 to 103 and a compound of the following chemical formula 2: Chemical formula 101 Chemical formula 102 Chemical formula 103 In the chemical formulas 101 to 103, Ar1 is a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthyl group. L1 is a directly bonded, substituted, or unsubstituted aryl group. X1 is either O or S. n1 is an integer from 0 to 3. One of R1 to R12 is connected to L1, and the others may be the same as or different from each other, and each is independently a hydrogen, deuterium, cyano, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. Chemical formula 2 In the chemical formula 2, D stands for deuterium. Ar11 and Ar12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Ar13 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. L11 and L12 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group. m1 is an integer from 0 to 7.

6. The organic light-emitting device according to claim 1, wherein, L1 can be a direct bond, or selected from any of the following structures: In the structure, The dashed line indicates the part connected to the chemical formula 1. The structure is substituted or unsubstituted by deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups.

7. The organic light-emitting device according to claim 1, wherein, Chemical Formula 1 is selected from one of the following compounds: 。 8. The organic light-emitting device according to claim 1, wherein, Chemical Formula 2 is selected from one of the following compounds: 。 9. The organic light-emitting device according to claim 1, wherein, The weight ratio of the compound of chemical formula 1 to the compound of chemical formula 2 is from 1:99 to 50:

50.

10. The organic light-emitting device according to claim 1, wherein, The luminescent layer comprises the compound of chemical formula 1 and the compound of chemical formula 2 as the main components.

11. The organic light-emitting device according to claim 1, wherein, The light-emitting layer also contains dopant substances. The dopant is an aromatic amine compound or a boron-containing polycyclic compound.

12. The organic light-emitting device according to claim 1, wherein, The luminescent layer comprises a first luminescent layer containing a compound of chemical formula 1 and a second luminescent layer containing a compound of chemical formula 2.

13. The organic light-emitting device according to claim 12, wherein, The second light-emitting layer is disposed between the first light-emitting layer and the cathode.

14. The organic light-emitting device according to claim 12, wherein, The first light-emitting layer and the second light-emitting layer are in contact with each other.

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