Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0043063 filed with the Korean Patent Office on March 31, 2023, the entire contents of which are incorporated into this specification.

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

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

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

[0005] Technical issues

[0006] The present specification provides a compound and an organic light-emitting device including the same.

[0007] Solution to the problem

[0008] This specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X1 and X2 are the same or different from each other and are each independently O or S,

[0013] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0014] wherein L1 is further substituted or unsubstituted by deuterium, hydroxyl, cyano, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and optionally, at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more substituted or unsubstituted rings,

[0015] One of R1 to R8 and R 101 To R 110 One of them is connected to L1, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and may be combined with adjacent substituents to form a substituted or unsubstituted ring,

[0016] m is an integer of 1 to 4. When m is 2 or more, L1 are the same or different from each other.

[0017] x is 1 or 2, y is 1 or 2,

[0018] When x and y are each 2, the structures in the brackets are the same as or different from each other.

[0019] In addition, the present specification provides an organic light-emitting device, characterized in that it includes: an anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers contains the above-mentioned compound.

[0020] Effects of the Invention

[0021] An organic light-emitting device using the compound according to one embodiment of the present application can achieve low driving voltage, high light-emitting efficiency, or long lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 The structure of the organic light emitting device according to the first embodiment is illustrated.

[0023] Figure 2 The structure of an organic light emitting device according to a second embodiment is illustrated.

[0024] Figure 3 The structure of an organic light emitting device according to a third embodiment is illustrated.

[0025] Figure 4 The structure of an organic light emitting device according to a fourth embodiment is illustrated.

[0026] Figure 5 This is a diagram showing the results of HPLC analysis of a film deposited using the mixture of Experimental Example 2.

[0027] Figure 6 This is a diagram showing the results of HPLC analysis of a film deposited using the mixture of Experimental Example 3.

[0028] <Description of symbols>

[0029] 101: Substrate

[0030] 102: Anode

[0031] 103: Hole injection layer

[0032] 104: Hole transport layer

[0033] 105: Hole regulation layer

[0034] 106: Luminous layer

[0035] 106-1: First light-emitting layer

[0036] 106-2: Second light-emitting layer

[0037] 107: Electronic Regulation Layer

[0038] 108: Electron transport layer

[0039] 109: Electron injection layer

[0040] 110: cathode DETAILED DESCRIPTION

[0041] Next, this specification is described in detail.

[0042] The present specification provides a compound represented by the above Chemical Formula 1.

[0043] According to the chemical formula 1 of one embodiment of the present specification, a structure in which benzo(thio)xanthene is bonded to a phenanthrofuran or phenanthiophene structure through an intermediate linking group L1, and the structure has excellent electron transfer and hole transfer capabilities and high quantum efficiency. Therefore, the compound of the chemical formula 1 is applied to the organic layer of an organic light-emitting device, and the effects of reduced driving voltage, improved efficiency, and long life can be seen.

[0044] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0045] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0046] In the present specification, * or a dotted line indicates a site that is bonded or fused to another substituent or a bonding part.

[0047] In this specification, Cn means that the number of carbon atoms is n, and Cn-Cm means that the number of carbon atoms is from n to m.

[0048] In the present specification, examples of substituents are described below, but are not limited thereto.

[0049] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0050] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano groups (-CN), silyl groups, boron groups, alkyl groups, cycloalkyl groups, aryl groups and heterocyclic groups, or substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent formed by connecting two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups.

[0051] In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a C1-C20 alkyl group, a C3-C60 cycloalkyl group, a C6-C60 aryl group, and a C2-C60 heterocyclic group, or substituted with a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0052] In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a C1-C20 alkyl group, a C3-C60 cycloalkyl group, a C6-C60 aryl group, and a C2-C60 heterocyclic group, or substituted with a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0053] In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a C1-C10 alkyl group, a C3-C30 cycloalkyl group, a C6-C30 aryl group, and a C2-C30 heterocyclic group, or substituted with a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0054] In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a silyl group, a C1-C6 alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group, and a C2-C20 heterocyclic group, or substituted with a substituent formed by connecting two or more groups selected from the above group, or having no substituents.

[0055] In this specification, two or more substituents are linked together means that the hydrogen of any substituent is replaced by another substituent. For example, isopropyl and phenyl can be linked together to form Such a substituent.

[0056] In this specification, three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, two phenyl groups and an isopropyl group can be connected to form The above description also applies to the case where four or more substituents are linked.

[0057] In the present specification, “substituted by A or B” includes not only the case of being substituted by A alone or the case of being substituted by B alone, but also the case of being substituted by both A and B.

[0058] In the present specification, "substituted with at least one selected from the group consisting of A, B and C" means substituted with one or more substituents selected from the above group, or substituted with a substituent formed by connecting two or more groups selected from the above group.

[0059] Examples of the above substituents are described below, but are not limited thereto.

[0060] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0061] In this specification, the silyl group can be represented by -SiY a Y b Y c The chemical formula of Y a , Y band Y c Each of them can be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The above-mentioned silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0062] In this specification, the boron group can be represented by -BY d Y e The chemical formula of Y d and Y e Each of them may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, and the like, but are not limited thereto.

[0063] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0064] The alkyl group and other substituents containing an alkyl moiety described in the present specification include all linear and branched forms.

[0065] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0066] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, Base, etc., but not limited to this.

[0067] In this specification, aryl can also include a form in which an aliphatic ring is fused to an aromatic ring. For example, fluorenyl, spirofluorenyl, spirobifluorenyl, tetrahydronaphthyl, dihydroindenyl or dihydroanthracenyl are included in aryl. In the following structure, one of the carbon atoms of the benzene ring can be connected to other positions.

[0068]

[0069] In the present specification, the carbon atom (C) No. 9 of the fluorenyl group may be substituted by an alkyl group, an aryl group or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

[0070] In the present specification, the above description about the aryl group is applicable to the arylene group except that the arylene group is a divalent group.

[0071] In the present specification, an alkylaryl group refers to an aryl group substituted by an alkyl group, and may further have a substituent other than the alkyl group bonded thereto.

[0072] In the present specification, an arylalkyl group refers to an alkyl group substituted with an aryl group, and may further have a substituent other than the alkyl group connected thereto.

[0073] In this specification, aryloxy is connected to an aryl group on an oxygen atom, and arylthio is connected to an aryl group on a sulfur atom. The aryl groups of aryloxy and arylthio can be applied to the above-mentioned description of aryl groups. The aryl group of aryloxy is the same as the exemplification of the above-mentioned aryl group. Specifically, as aryloxy, there are phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthraceneoxy, 2-anthraceneoxy, 9-anthraceneoxy, 1-phenanthrenoxy, 3-phenanthrenoxy, 9-phenanthrenoxy, etc., as arylthio, there are phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., but it is not limited thereto.

[0074] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuranyl, naphthobenzofuranyl, carbazolyl, benzocarbazolyl, naphthobenzothienyl, dibenzosilole, naphthobenzosilole, hexahydrocarbazolyl, dihydroacridinyl, dihydrodibenzoaziridinyl, phenanthrenyl, The alkyl radicals include phenoxazine, phenothiazine, dihydrodibenzodiazepine, spiro(dibenzosilole-dibenzodiazepine) and spiro(acridine-fluorene) and the like, but are not limited thereto.

[0075]

[0076] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0077] In the present specification, the amine group can be selected from -NH2, alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroarylamine and heteroarylamine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0078] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group.

[0079] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group.

[0080] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group.

[0081] In the present specification, the alkyl group, aryl group and heteroaryl group in the alkylamino group, N-alkylarylamino group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group and heteroarylamine group are the same as the examples of the alkyl group, aryl group and heteroaryl group described above, respectively.

[0082] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atoms substituted by the substituents, substituents closest to the substituents in stereostructure, or other substituents substituted on the atoms substituted by the substituents. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other. In addition, substituents connected to two consecutive carbons in an aliphatic ring (a total of 4) may also be interpreted as "adjacent" groups.

[0083] In the present specification, "adjacent groups in a substituent are bonded to each other to form a ring" means that adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0084] In the present specification, "a five-membered or six-membered ring formed by bonding adjacent groups" means that the ring including the substituents participating in the ring formation is a five-membered or six-membered ring. Another ring may be fused to the ring including the substituents participating in the ring formation.

[0085] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring or a combination thereof.

[0086] In the present specification, a heterocycle is a ring containing a heteroatom, and may be a ring containing a heteroatom and an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring condensed. The heterocycle may be an aromatic heterocycle, an aliphatic heterocycle, or a combination thereof.

[0087] In the present specification, an aromatic hydrocarbon ring refers to a planar hydrocarbon ring in which π electrons are completely conjugated, and the above description of the aryl group is applicable except that the aromatic hydrocarbon ring is divalent.

[0088] In this specification, an aliphatic hydrocarbon ring is a structure that is cyclically bonded, and refers to a ring that is not aromatic. Examples of aliphatic hydrocarbon rings include cycloalkyl or cycloalkane, and except for being divalent, the above description of the cycloalkyl or cycloalkenyl group can be applied. In addition, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0089] In the present specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring form a condensed ring. Examples of the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring include, but are not limited to, 1,2,3,4-tetrahydronaphthyl and 2,3-dihydro-1H-indenyl.

[0090] In the present specification, when adjacent groups in a substituent are bonded to each other to form a ring, any of the following structures may be formed.

[0091]

[0092] In the above structure,

[0093] A1 to A14 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0094] a1 to a9 are each an integer from 1 to 4,

[0095] a10 and a14 are each an integer from 1 to 6,

[0096] When a1 to a14 are each 2 or more, the two or more substituents in the brackets are the same or different from each other.

[0097] * indicates a substituted position.

[0098] According to one embodiment of the present specification, A1 is hydrogen or a substituted or unsubstituted aryl group.

[0099] According to one embodiment of the present specification, A1 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0100] According to one embodiment of the present specification, the above-mentioned A1 is hydrogen or a substituted or unsubstituted phenyl group.

[0101] According to one embodiment of the present specification, the above-mentioned A1 is hydrogen or phenyl.

[0102] According to one embodiment of the present specification, A2 to A10 and A14 are hydrogen.

[0103] According to one embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0104] According to one embodiment of the present specification, A11 to A13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0105] According to one embodiment of the present specification, A11 and A12 are methyl groups.

[0106] According to one embodiment of the present specification, the above-mentioned A13 is substituted or unsubstituted benzene, or substituted or unsubstituted naphthalene.

[0107] In this specification, the above x is 1, and the above y is 1.

[0108] In this specification, the above x is 1 and the above y is 2.

[0109] In this specification, the above x is 2 and the above y is 1.

[0110] In this specification, the above x is 2 and the above y is 2.

[0111] In the present specification, the above x is 1, the above y is 1, and the above L1 is the following chemical formula A or B.

[0112] [Chemical formula A]

[0113]

[0114] [Chemical formula B]

[0115]

[0116] In the above chemical formulas A and B,

[0117] X1 and X2 are the same or different from each other and are each independently O or S,

[0118] Two of R1 to R8 and R 101 To R 110 Two of them are each connected to an adjacent group, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may optionally be combined with adjacent substituents to form a substituted or unsubstituted ring,

[0119] * indicates the binding position.

[0120] In this specification, the above x is 1, the above y is 1, and the above R1 to R8 and R 101 To R 110 One of them is the following chemical formula A-1 or B-1.

[0121] [Chemical formula A-1]

[0122]

[0123] [Chemical formula B-1]

[0124]

[0125] In the above chemical formulas A-1 and B-1,

[0126] X1 and X2 are the same or different from each other and are each independently O or S,

[0127] Two of R1 to R8 and R 101 To R 110Two of them are each connected to an adjacent group, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may optionally be combined with adjacent substituents to form a substituted or unsubstituted ring,

[0128] * indicates the binding position.

[0129] In this specification, R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110 At least one of them may be combined to form a substituted or unsubstituted hydrocarbon ring.

[0130] In this specification, R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110 At least one of them may be combined to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

[0131] In this specification, R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110At least one of them may be combined to form a benzene ring which may be substituted by deuterium or a naphthalene ring which may be substituted by deuterium or not.

[0132] In this specification, R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110 At least one of them may be combined to form a substituted or unsubstituted benzene ring.

[0133] In this specification, R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110 At least one of them may be combined to form a benzene ring which may be substituted with deuterium or not.

[0134] In one embodiment of the present specification, the band gap energy of the above-mentioned compound may be greater than 2.9 eV, and may be greater than 2.9 eV and less than 4.0 eV. The organic compound used in the organic light-emitting device must have a band gap of 0.5 to 4.0 eV to function as an organic semiconductor. In order to display blue, a band gap energy of at least 2.9 eV is required. According to the fluorescent blue light-emitting principle of the host-dopant system, the band gap of the blue fluorescent host must be larger than the band gap of the blue fluorescent dopant in order to smoothly transfer energy. Therefore, in order to use the above-mentioned compound as a blue fluorescent host, it is preferred to have an energy band gap of 2.9 eV to 4.0 eV.

[0135] Various methods for calculating band gap energy are known, and in particular, cyclic voltammetry and absorption spectroscopy are representative.

[0136] Cyclic voltammetry is an electrochemical technique for measuring band gaps through oxidation (Oxidation) and reduction (Reduction) reactions of compounds. The current is measured under cyclic voltage conditions, and the oxidation-reduction reaction that occurs according to the change in potential energy is measured.

[0137] The absorption spectroscopy method measures UV-vis spectra, and is exemplified in Korean Patent Publication No. 2009-0051787 (KR2009-0051787A).

[0138] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0139] In the present specification, “overdeuterated” refers to a compound or group in which all hydrogen in the molecule is replaced by deuterium, and has the same meaning as “100% deuterated”.

[0140] In the present specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of hydrogen atoms at substitutable positions in the corresponding structure are substituted with deuterium. For example, when the corresponding structure is dibenzofuran, "25% deuterated" dibenzofuran, "deuteration degree 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogen atoms at substitutable positions of the dibenzofuran are substituted with deuterium.

[0141] In one embodiment of the present specification, the deuterium substitution rate of the above-mentioned compound can be 1% to 100%, specifically 40% to 99%. The deuterium substitution rate of the above-mentioned compound can be more than 5%, more than 10%, more than 20%, more than 30%, more than 40%, more than 50%, more than 60%, more than 70%, or more than 80% and less than 100%, or less than 99%. The physical and chemical properties such as the bond length of the chemical bond related to deuterium show that it is different from hydrogen. In particular, compared with the CH bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Under normal circumstances, it can be shown that the CD bond is shorter and stronger than the CH bond. When replaced by deuterium, the energy of the ground state is reduced, and the bond length of deuterium and carbon becomes shorter, so the molecular hardcore volume is reduced. Therefore, the electrical polarizability can be reduced, and the interaction between molecules can be weakened, so that the film volume can be increased.

[0142] Such characteristics can produce an effect of reducing the crystallinity of the film, that is, an amorphous state, which can generally effectively improve the lifespan and driving characteristics of the OLED and can further improve the heat resistance.

[0143] As prior arts related to the above-mentioned deuterium-containing organic light-emitting compounds, Korean Patent Gazette No. 10-1111406 describes a technology for providing low-voltage drive and long-life devices by replacing an amine compound containing a carbazole group with deuterium, or mixing a compound substituted with deuterium, and Korean Patent Gazette No. 10-1068224 describes a technology for using an anthracene derivative containing a phenyl group in which hydrogen in the phenyl group is substituted with deuterium as a main body.

[0144] Among them, the deuterium substitution rate can be calculated using the spectrum obtained by mass spectrometry of the substance separated by column chromatography. Specifically, the deuterium substitution rate can be calculated based on the maximum value of the distribution composed of molecular weight in the spectrum obtained by mass spectrometry of the substance separated by liquid chromatography or gas chromatography according to the sample to be measured. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506. When the maximum molecular weight (intermediate value) of the following compound A in the MS spectrum is 527, 21 of the hydrogens (26) at the substitutable positions of the following starting material are replaced by deuterium, so it can be calculated that about 81% of the hydrogen is deuterated.

[0145]

[0146] In this specification, D represents deuterium.

[0147] Another method for determining the deuterium substitution rate is to use nuclear magnetic resonance (NMR). Specifically, DMF (dimethylformamide) can be added as an internal standard. 1 The deuterium substitution rate was calculated from the integration ratio of the H NMR spectrum and the integrated amount of the total peak.

[0148] In one embodiment of the present specification, the compound of the above Chemical Formula 1 may be any one of the following structures.

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] The hydrogen in the above structure may be replaced by deuterium.

[0168] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0169] In one embodiment of the present specification, an organic light-emitting device is provided, including: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the compound.

[0170] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0171] In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

[0172] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound. Specifically, the light-emitting layer may include a host and a dopant including the compound.

[0173] In one embodiment of the present specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

[0174] In one embodiment of the present specification, the organic layer includes a light-emitting layer and further includes one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

[0175] In one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, the organic layer includes: a light-emitting layer, a hole transport region arranged between the light-emitting layer and the anode, and an electron transport region arranged between the light-emitting layer and the cathode, and the light-emitting layer contains the above-mentioned compound.

[0176] In one embodiment of the present specification, the organic layer in the hole transport region may be selected from one or more of the group consisting of a hole transport layer, a hole injection layer, a layer that simultaneously transports and injects holes, and an electron blocking layer.

[0177] In one embodiment of the present specification, the organic layer in the electron transport region may be selected from one or more of the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

[0178] In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0179] In another embodiment, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

[0180] For example, the organic light emitting device may have a stacked structure as described below, but is not limited thereto.

[0181] (1) Anode / hole transport layer / light-emitting layer / cathode

[0182] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0183] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0184] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0185] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0186] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0187] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0188] (8) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0189] (9) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0190] (10) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0191] (11) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0192] (12) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / cathode

[0193] (13) Anode / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0194] (14) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / cathode

[0195] (15) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron transport layer / electron injection layer / cathode

[0196] (16) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / cathode

[0197] (17) Anode / hole injection layer / hole transport layer / hole regulation layer / first light emitting layer / second light emitting layer / electron transport layer / electron injection layer / cathode

[0198] (18) Anode / hole injection layer / hole transport layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0199] (19) Anode / hole injection layer / hole transport layer / hole regulation layer / first light-emitting layer / second light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0200] The structure of the organic light-emitting device of the present specification may have the following Figures 1 to 4 The structure shown is not limited to this.

[0201] Figure 1 An example of an organic light-emitting device according to an embodiment of the present specification is shown, illustrating a 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 above structure, the compound of Chemical Formula 1 and the second compound as an anthracene derivative may be contained in a single-layer light-emitting layer as a mixture or a combination, or may be contained in two light-emitting layers.

[0202] Figure 2 An example of an organic light-emitting device according to an embodiment of the present specification is shown, and a structure of an organic light-emitting device is shown in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked. In the above structure, the compound of the above Chemical Formula 1 and the second compound which is an anthracene derivative may be included in a single-layer light-emitting layer 105 or in two-layer light-emitting layers 105, respectively.

[0203] Figure 3 An example of an organic light-emitting device according to an embodiment of the present specification is shown, and the structure of the organic light-emitting device is shown, which sequentially stacks a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole regulation layer 105, a light-emitting layer 106, an electron regulation layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110. In the above structure, the compound of the above Chemical Formula 1 and the second compound which is an anthracene derivative may be included in a single-layer light-emitting layer or respectively included in two or more light-emitting layers.

[0204] Figure 4An example of an organic light-emitting device according to an embodiment of the present specification is shown, and the structure of the organic light-emitting device is sequentially stacked with a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a hole adjustment layer 105, a first light-emitting layer 106-1, a second light-emitting layer 106-2, an electron adjustment layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110. In the above structure, the compound of the above chemical formula 1 may be included in the first light-emitting layer 106-1. Alternatively, the second compound as an anthracene derivative may be included in the second light-emitting layer 106-2, or vice versa.

[0205] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that one or more layers of the organic material layer contain the compound of the present specification, that is, the above-mentioned compound.

[0206] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0207] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that at least one layer of the organic material layer contains the compound represented by the above Chemical Formula 1.

[0208] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, it can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0209] In addition, the compound of the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0210] The anode is an electrode for injecting holes. As an anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0211] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0212] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0213] According to one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-1, but is not limited thereto.

[0214] [Chemical formula HI-1]

[0215]

[0216] In the above chemical formula HI-1,

[0217] At least one of X'1 to X'6 is N, and the others are CH,

[0218] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0219] According to one embodiment of the present specification, X'1 to X'6 are N.

[0220] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0221] According to one embodiment of the present specification, the chemical formula HI-1 is the following compound.

[0222]

[0223] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0224] The hole regulating layer is a layer that regulates the holes transferred from the hole transport layer to be smoothly injected into the light-emitting layer, and prevents the electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0225] According to one embodiment of the present specification, the hole transport layer or the hole regulation layer includes a compound of the following chemical formula HT-1, but is not limited thereto.

[0226] [Chemical formula HT-1]

[0227]

[0228] In the above chemical formula HT-1,

[0229] R315 to R317 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0230] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0231] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0232] According to one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0233] According to one embodiment of the present specification, the R317 is any one selected from a carbazolyl group, a phenyl group, a biphenyl group, and a combination thereof.

[0234] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0235] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or phenanthryl, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0236] According to one embodiment of the present specification, the chemical formula HT-1 is any one of the following compounds.

[0237]

[0238] The electron regulating layer is a layer for regulating smooth injection of electrons transferred from the electron transporting layer into the light emitting layer, and any known material can be used without limitation.

[0239] According to one embodiment of the present specification, the electron adjustment layer includes a compound of the following chemical formula EG-1, but is not limited thereto.

[0240] [Chemical formula EG-1]

[0241]

[0242] In the above chemical formula EG-1,

[0243] At least one of G'1 to G'18 is -L5-Ar5, and the others are hydrogen, or G'1 and G'18 are connected through -L51- to form a substituted or unsubstituted ring,

[0244] L5 is a direct bond, or a substituted or unsubstituted arylene group,

[0245] Ar5 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0246] L51 is O or S.

[0247] According to one embodiment of the present specification, the above-mentioned L51 is O.

[0248] According to one embodiment of the present specification, the above-mentioned L51 is S.

[0249] According to one embodiment of the present specification, the above G'1 and G'18 are linked via -L51- to form a substituted or unsubstituted heterocyclic ring.

[0250] According to one embodiment of the present specification, the above G'1 and G'18 are linked via -L51- to form a substituted or unsubstituted xanthene ring or a substituted or unsubstituted thioxanthene ring.

[0251] According to one embodiment of the present specification, the above G'1 and G'18 are linked via -O- to form a substituted or unsubstituted xanthene ring.

[0252] According to one embodiment of the present specification, the above G'1 and G'18 are linked by -S- to form a substituted or unsubstituted thioxanthene ring.

[0253] According to one embodiment of the present specification, the G'1 and G'18 are linked via -O- to form a xanthene ring.

[0254] According to one embodiment of the present specification, the G'1 and G'18 are linked via -S- to form a thioxanthene ring.

[0255] According to one embodiment of the present specification, the above-mentioned L5 is a directly bonded or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0256] According to one embodiment of the present specification, the above-mentioned L5 is a directly bonded or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0257] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0258] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0259] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond or a phenylene group.

[0260] According to one embodiment of the present specification, the Ar5 is a substituted or unsubstituted triazine group.

[0261] According to one embodiment of the present specification, Ar5 is a triazine group which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0262] According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

[0263] According to one embodiment of the present specification, the above-mentioned EG-1 is the following compound.

[0264]

[0265] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the weight ratio of the host to the dopant is 0.1:99.9 to 20:80.

[0266] The main material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are carbazole derivatives, dibenzofuran, dibenzofuran derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds. Pyrimidine derivatives, etc., but are not limited to these.

[0267] As for the dopant of the light-emitting layer, when the light-emitting layer emits red light, as the light-emitting dopant, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum); or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum), but not limited to these can be used. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.

[0268] In one embodiment of the present specification, the light-emitting layer includes one or more first compounds of Chemical Formula 1 of the present application and a second compound that is an anthracene derivative.

[0269] In one embodiment of the present specification, the light-emitting layer may be composed of a single layer, but may be composed of two or more layers.

[0270] When the light-emitting layer is a single layer, it contains the first compound of Chemical Formula 1 and the second compound which is an anthracene derivative in one layer. Such a single-layer light-emitting layer can be formed by co-evaporation of the first compound of Chemical Formula 1 and the second compound which is an anthracene derivative.

[0271] When the light-emitting layer is a plurality of layers of two or more, the first compound of the chemical formula 1 and the second compound as an anthracene derivative may be contained in one layer, or the first compound of the chemical formula 1 and the second compound as an anthracene derivative may be contained in different light-emitting layers. For example, the light-emitting layer may include a first light-emitting layer containing the first compound of the chemical formula 1 and a second light-emitting layer containing the second compound as an anthracene derivative. 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 the chemical formula 1 and the second compound as an anthracene derivative as a main body, the first light-emitting layer and the second light-emitting layer each further contain a dopant compound. In this case, the first light-emitting layer and the second light-emitting layer may contain the same kind of dopant substance or different kinds of dopant substances, but preferably contain the same kind of dopant substances.

[0272] In one embodiment of the present specification, the one or more light-emitting layers contain the compound of the above Chemical Formula 1 and a second compound that is an anthracene derivative as a host.

[0273] In one embodiment of the present specification, the second compound as an anthracene derivative may include at least one of the compound of the following Chemical Formula 2 and the compound of the following Chemical Formula 3. Specifically, the second compound as an anthracene derivative is a mixed body including two different anthracene derivatives, and may include the compound of the following Chemical Formula 2 and the compound of the following Chemical Formula 3.

[0274] [Chemical formula 2]

[0275]

[0276] In the above chemical formula 2,

[0277] At least one of R11 to R20 is bonded to the * site of the following chemical formula 2-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0278] [Chemical formula 2-1]

[0279]

[0280] In the above chemical formula 2-1,

[0281] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0282] Ar2 is a substituted or unsubstituted aryl group,

[0283] p is an integer from 1 to 3,

[0284] [Chemical formula 3]

[0285]

[0286] In the above chemical formula 3,

[0287] At least one of Y1 to Y10 is bonded to the * site of the following chemical formula 3-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0288] [Chemical formula 3-1]

[0289]

[0290] In the above chemical formula 3-1,

[0291] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0292] L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0293] q is an integer from 1 to 3.

[0294] The present inventors have discovered suitable conditions for a phenanthrofuran or phenanthiophene type host (hereinafter, compound of Chemical Formula 1) and an anthracene type host (hereinafter, compounds of Chemical Formulas 2 and 3) that are both useful as blue fluorescent host substances and can simultaneously provide a stable co-evaporation mixture after premixing.

[0295] The light-emitting layer of an organic light-emitting device that shows excellent life and efficiency requires more than 2 components (for example, 3 or 4 components). For this purpose, it is required to manufacture such a light-emitting layer with 3 or 4 raw materials, which is very complicated and costly compared to a standard two-component light-emitting layer with a single host and a dopant that only requires 2 raw materials. Premixing more than 2 substances and evaporating them from one raw material can reduce the complexity of the manufacturing process. The selected hole transport host and other types of hosts (such as electron transport hosts) can be mixed and co-evaporated in one crucible, so that stable evaporation can be achieved.

[0296] However, the co-evaporation must be stable, i.e. the composition of the evaporated film must remain constant during the manufacturing process. Any compositional changes may have an adverse effect on the device performance. In order to obtain a stable co-evaporation based on a mixture of compounds under vacuum, it can be assumed that the substances should have the same evaporation temperature under the same conditions. However, this should not be the only parameter to be considered. When two compounds are mixed together, they can interact with each other and their evaporation characteristics can differ from their individual characteristics. On the other hand, substances with slightly different evaporation temperatures can generate stable co-evaporated mixtures. Therefore, it is extremely difficult to achieve stable co-evaporated mixtures. To date, although there are tens of thousands of usable host substances in the literature, there are very few examples of stable co-evaporated mixtures. The "evaporation temperature" of a substance is the temperature at which the evaporated substance evaporates on a surface at a set distance from the evaporation source of the evaporated substance. The evaporation rate is 1×10 -6 Torr to 1×10 -9 The various measured values ​​described in this specification, such as temperature, pressure, evaporation rate, etc., are expected to have nominal variations due to expected fair errors in the determination of the calculated quantitative values, as understood by those skilled in the art.

[0297] In the disclosure of this specification, a new type of two different types of anthracene hosts (chemical formulas 2 and 3) that are premixed and useful as blue fluorescent host materials and can provide a stable co-evaporation mixture is described. Multiple factors other than temperature can contribute to evaporation, for example, the miscibility of different substances, different phase transitions. The inventors have found that when two substances have similar evaporation temperatures, similar mass reduction rates or similar vapor pressures, the two substances can be continuously co-evaporated. The mass reduction rate is defined as the percentage of mass reduction change according to time (minutes), as measured by thermogravimetric analysis (TGA) under the same experimental conditions at the same given constant temperature for each compound after the composition reaches a normal evaporation state, and is determined by measuring the time required for the initial 10% mass reduction. The given constant temperature is a temperature point selected in such a way that the mass reduction rate value becomes about 0.05% / minute to 0.50% / minute. Those skilled in the art will understand that in order to compare two parameters, the experimental conditions must be constant. The method of measuring the mass reduction rate and the vapor pressure is known in the art, and can be found in, for example, the document “Bull. et al. Mater. Sci. 2011, 34, 7”.

[0298] Under the state of the art, in the mixing of two components of the blue fluorescent host, the prior art document of the present invention is disclosed in the suggested JP6328890B2. In order to produce a blue fluorescent light-emitting layer having such a mixed host substance, three evaporation sources are required: two hosts and a blue fluorescent dopant. The concentration of the co-host and the dopant is important for the device performance. Usually, the evaporation rate of each component is measured separately during the evaporation process. This will make the manufacturing process complicated and costly. Therefore, it is preferred to mix more than two components to reduce the amount of raw materials.

[0299] When two blue fluorescent hosts are premixed and the mixture is made by thermal sublimation, if the difference in composition is below a certain range, it means that they can be co-evaporated from one raw material. Uniform co-evaporation of the two hosts is important for the performance sustainability of the device made from the mixture.

[0300] Next, the compound of Chemical Formula 2 is described in detail.

[0301] According to one embodiment of the present specification, 1 to 3 of the above R11 to R20 are bound to the * site of the above chemical formula 2-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0302] According to another embodiment, 1 to 3 of the above R11 to R20 are bound to the * site of the above chemical formula 2-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0303] In another embodiment, the above R19 and R20 are bound to the * portion of the above Chemical Formula 2-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0304] According to another embodiment, the above R19, R20 and R18 are bound to the * portion of the above Chemical Formula 2-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0305] In another embodiment, the above R19, R20 and R17 are bound to the * portion of the above Chemical Formula 2-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0306] According to one embodiment of the present specification, the substituents in R11 to R20 that are not bound to the chemical formula 2-1 are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl.

[0307] According to one embodiment of the present specification, the above p is an integer of 3, and the three L2s are the same as or different from each other.

[0308] In another embodiment, the above p is an integer of 2, and the two L2 are the same as or different from each other.

[0309] According to one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0310] In another embodiment, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0311] According to another embodiment, L2 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0312] In another embodiment, L2 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0313] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar2 may be substituted with deuterium.

[0314] In another embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0315] According to another embodiment, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0316] In another embodiment, Ar2 is phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0317] The compound of the above Chemical Formula 2 may be compounds described in JP4070676B2, KR1477844B1, US6465115B2, JP3148176B2, JP4025136B2, JP4188082B2, JP5015459B2, KR1979037B1, KR1550351B1, KR1503766B1, KR0826364B1, KR0749631B1, KR1115255B1, KR1538534B1, and the like.

[0318] Next, the compound of Chemical Formula 3 is described in detail.

[0319] According to one embodiment of the present specification, at least one of the above Y1 to Y10 is bonded to the * site of the above chemical formula 3-1, and the others are the same or different from each other and are independently hydrogen, deuterium, or a substituted or unsubstituted aromatic group having 6 to 60 carbon atoms.

[0320] According to one embodiment of the present specification, one to three of the above Y1 to Y10 are bound to the * site of the above Chemical Formula 3-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0321] In one embodiment of the present specification, one to three of the above Y1 to Y10 are bound to the * portion of the above Chemical Formula 3-1, and the rest are the same or different from each other and are independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0322] In another embodiment, the above-mentioned Y7, Y8 or Y9 is bound to the * position of the above-mentioned chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0323] According to another embodiment, the above-mentioned Y7 and Y9 are bound to the * position of the above-mentioned chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0324] According to another embodiment, the above-mentioned Y9 and Y10 are bound to the * position of the above-mentioned chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0325] According to one embodiment of the present specification, the substituents not bonded to the above Chemical Formula 3-1 among Y1 to Y10 are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The substituents not bonded to the above Chemical Formula 2-1 among Y1 to Y10 may be substituted with deuterium.

[0326] According to another embodiment, the substituents in the above Y1 to Y10 that are not combined with the above Chemical Formula 3-1 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted triphenylene, and the above substituents may be further substituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0327] In one embodiment of the present specification, the above q is an integer of 1 to 3, and when the above q is 2 or more, two or more L3 are the same as or different from each other.

[0328] According to one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0329] In another embodiment, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0330] According to another embodiment, L3 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0331] In another embodiment, L3 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0332] According to one embodiment of the present specification, A and B are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms.

[0333] In one embodiment of the present specification, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium.

[0334] According to another embodiment, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium.

[0335] In another embodiment, A and B are the same as or different from each other, and are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, or substituted or unsubstituted dibenzofuran.

[0336] According to another embodiment, A and B are the same as or different from each other, and are each independently benzene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, naphthalene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, phenanthrene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, triphenylene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, or dibenzofuran substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium.

[0337] The compound of the above Chemical Formula 3 may be a compound described in KR1964435B1, KR1899728B1, KR1975945B1, KR2018-0098122A, KR2018-0102937A, KR2018-0103352A, KR1538534B1, etc.

[0338] In the organic light-emitting device according to one embodiment of the present specification, the sublimation temperature (T sub1 ) and the sublimation temperature (T sub2 ) satisfies the following formula (1):

[0339] |T sub1 –T sub2 | ≤ 20℃ - Formula (1)

[0340] When the above-mentioned constitution is satisfied, the low voltage and high efficiency provided by the above-mentioned second compound are reproduced, and at the same time, the electron injection to the triplet energy level provided by the above-mentioned first compound of Chemical Formula 1 becomes easy, so that the formation ratio of excitons is improved, thereby having the advantage of improving the luminous efficiency.

[0341] In the organic light-emitting device according to one embodiment of the present specification, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0342] The first light-emitting layer comprises the compound of the chemical formula 1 as a first host material,

[0343] The second light-emitting layer includes at least one of the compounds of Chemical Formulae 2 and 3 as a second host material. When such a structure is satisfied, the efficiency of the organic light-emitting device can be further improved.

[0344] In the organic light-emitting device according to one embodiment of the present specification, the second light-emitting layer is provided between the first light-emitting layer and the cathode.

[0345] In the organic light-emitting device according to one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer are provided in direct contact with each other. When such a structure is satisfied, the efficiency of the organic light-emitting device can be further improved.

[0346] In the organic light-emitting device according to one embodiment of the present specification, the first light-emitting layer includes a combination of two or more compounds of the chemical formula 1 as the first host material.

[0347] In the organic light-emitting device according to one embodiment of the present specification, the light-emitting layer further includes a dopant substance.

[0348] As described above, the light-emitting layer may include a single layer or more than two light-emitting layers. When the light-emitting layer is a single layer, the compound of Chemical Formula 1 and the second compound as an anthracene derivative may further include a single dopant substance or a combination of multiple dopant substances. In addition, when the light-emitting layer is a double layer, including a first light-emitting layer including the compound of Chemical Formula 1 and a second light-emitting layer including the second compound as an anthracene derivative, each light-emitting layer may include the same type of dopant substance as each other, or may include different types of dopant substances as each other. Preferably, the same type of dopant substances are included in the light-emitting layers of more than two layers.

[0349] In the organic light-emitting device according to one embodiment of the present specification, the dopant substance is a fluorescent dopant.

[0350] In the organic light-emitting device according to one embodiment of the present specification, the fluorescent dopant is a blue fluorescent dopant.

[0351] In the organic light-emitting device according to one embodiment of the present specification, the blue fluorescent dopant is a pyrene based compound or a non-pyrene based compound.

[0352] In the organic light-emitting device according to one embodiment of the present specification, the non-pyrene-based compound is an arylamine-based compound or a boron-based compound.

[0353] Compared with the above-mentioned pyrene compounds, when non-pyrene compounds are used as fluorescent dopants, the efficiency can be improved and the life span can be increased due to the narrow half-width characteristics.

[0354] The above-mentioned pyrene-based compound can be a pyrene-based compound substituted with a diarylamine, such as BD02 (N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine), which has a smaller band gap than the host substance.

[0355] The above-mentioned non-pyrene compounds are compounds that are not pyrene or pyrene derivatives, and can include metal complexes (iridium complexes, platinum complexes, etc.), boron compounds (DABNA-1, etc.), aromatic amine compounds (coumarin 6, etc.), etc., but are not limited to these.

[0356] In one embodiment of the present specification, the pyrene-based compound may be represented by the following chemical formula Z1, and the non-pyrene-based compound may be represented by the following chemical formulas Z2 (arylamine-based compound) and Z3 (boron-based compound).

[0357] [Chemical formula Z1]

[0358]

[0359] [Chemical formula Z2]

[0360]

[0361] [Chemical formula Z3]

[0362]

[0363] In the above chemical formulae Z1 to Z3,

[0364] X3 and X4 are each hydrogen or deuterium, or directly bond to each other to form a ring,

[0365] R41 and R42 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

[0366] Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0367] Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring, or a monocyclic to polycyclic aromatic heterocyclic ring,

[0368] R31, R32, R43 to R46 and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent substituents to form a substituted or unsubstituted ring,

[0369] R41, R42 and R51 to R53 are each an integer of 0 to 4, and when the integer is 2 or more, the substituents in the brackets are the same as or different from each other.

[0370] In one embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0371] In one embodiment of the present specification, Ar31 to Ar34, Ar41 to Ar44, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6-C20 aryl group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C6 alkyl group, or a substituent formed by connecting two or more groups selected from the above group; or a C2-C20 heterocyclic group substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C6 alkyl group, or a substituent formed by connecting two or more groups selected from the above group.

[0372] In one embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other, and are each independently a monocyclic to tricyclic aromatic hydrocarbon ring; or a monocyclic to tricyclic aromatic heterocyclic ring containing N, O or S.

[0373] In one embodiment of the present specification, Cy1 to Cy3 are the same as or different from each other, and are each 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 condensed with a C5-C10 aliphatic hydrocarbon ring.

[0374] In one embodiment of the present specification, R31, R32, R43 to R46, and R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted 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 are combined with adjacent substituents to form a C3-C30 hydrocarbon ring, or a substituted or unsubstituted C2-C30 heterocyclic ring.

[0375] In one embodiment of the present specification, R31 and R32 are hydrogen or deuterium.

[0376] In one embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0377] In one embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted by an alkyl group, or a substituted or unsubstituted C2-C30 O-containing heterocyclic group.

[0378] In one embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a phenyl group which may be substituted or unsubstituted by an alkyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0379] In one embodiment of the present specification, the chemical formula Z3 as the boron-based compound is any one of the following chemical formulas Z3-1 to Z3-3.

[0380] [Chemical formula Z3-1]

[0381]

[0382] [Chemical formula Z3-2]

[0383]

[0384] [Chemical formula Z3-3]

[0385]

[0386] In the above chemical formulas Z3-1 to Z3-3,

[0387] R51 to R53, r52, Ar51 and Ar52 are the same as defined in the chemical formula Z3,

[0388] X5 is O or S,

[0389] r521 is an integer from 0 to 2. When r521 is 2, R52 are the same as or different from each other.

[0390] In one embodiment of the present specification, Ar51 and Ar52 are the same as or different from each other, and are each independently a C6-C30 aryl group fused with or not fused with an aliphatic hydrocarbon ring, or a C2-C30 heterocyclic group, and the above aryl group or heterocyclic group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C10 alkyl group, or a substituent formed by connecting two or more groups selected from the above group.

[0391] In one embodiment of the present specification, the aryl group or heterocyclic group of Ar51 includes a substituent other than hydrogen at a position that is para-oriented relative to the nitrogen to which it is connected.

[0392] In one embodiment of the present specification, the aryl group or heterocyclic group of Ar52 includes a substituent other than hydrogen at a position that is para-oriented relative to the nitrogen to which it is connected.

[0393] In one embodiment of the present specification, R51 to R53 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted 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 are combined with adjacent substituents to form a C3-C30 aliphatic hydrocarbon ring, or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

[0394] In one embodiment of the present specification, R51 to R53 are the same as or different from each other, and are independently hydrogen, deuterium, methyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, diphenylamino, or bis((tert-butyl)phenyl)amino.

[0395] In one embodiment of the present specification, two adjacent R51, two adjacent R52, or two adjacent R53 are combined 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 a cyclopentene, cyclohexene, tetralin, benzene or naphthalene ring.

[0396] In one embodiment of the present specification, the dopant may be selected from the following structures, but is not limited thereto.

[0397]

[0398] In one embodiment of the present specification, in the light-emitting layer, based on 100 parts by weight of the host material, the dopant material may be contained in an amount of 0.01 to 50 parts by weight, and may be contained in an amount of 0.1 to 30 parts by weight, 1 to 10 parts by weight, or 2 parts by weight. Within the above range, energy transfer from the host to the dopant occurs effectively. At this time, 100 parts by weight of the host material is based on the total weight of the compound of the above chemical formula 1 and / or the second compound.

[0399] When the above configuration is met, the efficiency of the organic light-emitting device can be further improved.

[0400] In the organic light-emitting device according to one embodiment of the present specification, a deuterium substitution rate of at least one of the first compound of Chemical Formula 1 and the second compound is each independently 1% or more and 100% or less.

[0401] In one embodiment of the present specification, the deuterium substitution rate of at least one of the first compound of Chemical Formula 1 and the second compound may be independently 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more.

[0402] In one embodiment of the present specification, the deuterium substitution rate of at least one of the first compound of Chemical Formula 1 and the second compound may be independently 100% or less, 99% or less, 98% or less, 97% or less, 96% or less, or 95% or less.

[0403] According to one embodiment of the present specification, the deuterium substitution rates of both the first compound of Chemical Formula 1 and the second compound are 100%.

[0404] The above-mentioned deuterium substitution rate can be calculated by the above-mentioned method. According to another example, at least one deuterium is directly substituted on the above-mentioned second compound. The light-emitting layer of the organic light-emitting device, as the region of light emission, is an interval where the energy-induced molecular loss is large. The carbon-deuterium bond is stronger than the carbon-hydrogen bond, and deuterium has a higher mass value than hydrogen, which reduces the zero point energy with carbon, so that the bond energy is high. Therefore, the carbon-hydrogen bond contained in the molecule of the compound of the above-mentioned chemical formula 2 is replaced by a carbon-deuterium bond to increase the bond energy of the molecule, so that a device with excellent life can be obtained.

[0405]

[0406] The organic light emitting device including the chemical formula 1 and / or the second compound having the deuterium substitution rate according to one embodiment of the present specification has improved heat resistance, having the effect of improving lifespan.

[0407] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) is above 2.30 eV.

[0408] In one embodiment of the present specification, the triplet energy level (T h1 ) can be greater than 2.30 eV, greater than 2.40 eV, or greater than 2.50 eV.

[0409] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1) is greater than the triplet energy level (T h2 )high.

[0410] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) can satisfy 2.30eV≤T h1 ≤2.90eV.

[0411] In one embodiment of the present specification, the triplet energy level (T h1 ) may be greater than 2.30 eV, greater than 2.40 eV, or greater than 2.50 eV.

[0412] In one embodiment of the present specification, the triplet energy level (T h1 ) can be less than 2.90 eV, less than 2.80 eV, or less than 2.70 eV.

[0413] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h2 ) can satisfy 1.40eV≤T h2 ≤1.80eV.

[0414] In one embodiment of the present specification, the triplet energy level (T h2 ) may be greater than 1.40 eV, greater than 1.45 eV, greater than 1.50 eV, or greater than 1.55 eV.

[0415] In one embodiment of the present specification, the triplet energy level (T h2 ) can be less than 1.80 eV, less than 1.75 eV, less than 1.70 eV, or less than 1.65 eV.

[0416] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T h2 ) can satisfy the following formula (2).

[0417] Δ(T h1 -T h2 )≤ 1.50eV - Formula (2)

[0418] In one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T h2 ) difference (Δ(T h1 -Th2 )) can be below 1.50 eV, below 1.45 eV, below 1.40 eV, below 1.35 eV, or below 1.30 eV.

[0419] In the organic light-emitting device according to one embodiment of the present specification, the triplet energy level (T h1 ), the triplet energy level of the second compound (T h2 ) and the triplet energy level (T BD ) can satisfy at least one of the following formulas (3) and (4).

[0420] Δ(T BD -T h1 )≤0.40eV-Formula (3), and

[0421] Δ(T BD -T h2 )≥0.40eV- Formula (4)

[0422] In one embodiment of the present specification, the triplet energy level (T h1 ) and the triplet energy level (T BD ) difference (Δ(T BD -T h1 )) can be below 0.40 eV, below 0.35 eV, or below 0.30 eV.

[0423] In one embodiment of the present specification, the triplet energy level (T h2 ) and the triplet energy level (T BD ) difference (Δ(T BD -T h2 )) can be greater than 0.40 eV, greater than 0.45 eV, or greater than 0.50 eV.

[0424] When any one of the above-mentioned configurations is satisfied, electron injection into the triplet level of the dopant is facilitated, and the formation ratio of excitons is increased, thereby improving efficiency.

[0425] In this specification, the triplet energy level (T h1 ) can be measured using a spectrometer capable of measuring fluorescence and phosphorescence. As for the measurement conditions, a concentration of 10 -6M solution, irradiating the solution with a light source in the absorption wavelength range of the substance, excluding singlet emission from the emission spectrum, and analyzing and confirming the spectrum of triplet emission. When electrons are excited by the light source, the time they stay in the triplet state is much longer than the time they stay in the singlet state, so the two components can be separated at extremely low temperatures.

[0426] In this specification, triplet energy (E T1 ) can be calculated by the following method. After cooling the sample to 77K, irradiate the sample for phosphorescence measurement with excitation light (360nm), measure the phosphorescence intensity using a streak camera, draw a tangent to the rising point of the phosphorescence spectrum, and find the wavelength value λedge [nm] of the intersection of the tangent and the x-axis. Substitute this wavelength value into the following formula (6), and the energy value E can be calculated. T1 At this time, the emission spectrum was measured using a nitrogen molecule laser (manufactured by Lasertechnik Berlin, MNL200) and a streak camera (manufactured by Hamamatsu Photonics, C4334).

[0427] E T1 [eV] = 1239.85 / λedge - Formula (6)

[0428] In one embodiment of the present specification, the triplet energy level (E T1 ) can be calculated using Gaussian 03, a quantum chemical calculation program manufactured by Gaussian Corporation of the United States. Specifically, for a structure optimized using density functional theory (DFT) using B3LYP (Becke, three-parameter, Lee-Yang-Parr) as a functional and 6-31G* as a basis function, the calculated value of the triplet energy can be obtained by time-dependent density functional theory (TD-DFT).

[0429] In the organic light-emitting device according to one embodiment of the present specification, in the light-emitting layer, the maximum emission wavelengths (λmax) of the compound of Chemical Formula 1 and the second compound may each be within a range of 400 nm to 500 nm.

[0430] Preferably, the maximum emission wavelength (λmax) of the compound of Chemical Formula 1 and the second compound may each be within a range of 400 nm to 485 nm, or 400 nm to 470 nm. When such a configuration is satisfied, the light-emitting layer may emit blue light.

[0431] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., 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, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, and in each case, they are accompanied by an aluminum layer or a silver layer.

[0432] According to one embodiment of the present specification, the electron transport layer includes a compound of the following chemical formula ET-1, but is not limited thereto.

[0433] [Chemical formula ET-1]

[0434]

[0435] In the above chemical formula ET-1,

[0436] At least one of Z11 to Z13 is N, and the rest are CH,

[0437] L601 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0438] Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0439] l601 is an integer from 1 to 5. When the above l601 is 2 or more, the above two or more L601 are the same as or different from each other.

[0440] According to one embodiment of the present specification, the above L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0441] According to one embodiment of the present specification, the L601 is a phenylene group, a biphenylene group, or a naphthylene group.

[0442] According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0443] According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

[0444] According to one embodiment of the present specification, the chemical formula ET-1 is the following compound.

[0445]

[0446] The electron injection layer is a layer for injecting electrons from the electrode, and preferably uses the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0447] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0448] The above-mentioned covering layer is formed to prevent a large amount of light from being lost through total reflection of light in the organic light-emitting device. The covering layer has the property of fully protecting the lower cathode and the light-emitting layer from external moisture penetration or contamination. It has a high refractive index and can prevent light loss due to total reflection, and existing materials can be used without restrictions.

[0449] According to one embodiment of the present specification, the cover layer includes a compound of the following chemical formula CP-1, but is not limited thereto.

[0450] [Chemical formula CP-1]

[0451]

[0452] In the above chemical formula CP-1,

[0453] L501 and L502 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0454] R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0455] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0456] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0457] According to one embodiment of the present specification, the above R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0458] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are combined with adjacent groups to form carbazole substituted or unsubstituted with a phenyl group.

[0459] According to one embodiment of the present specification, Ar501 and L501 are bonded to form a carbazole substituted with a phenyl group.

[0460] According to one embodiment of the present specification, Ar503 and L503 are bonded to form a carbazole substituted with a phenyl group.

[0461] According to one embodiment of the present specification, the chemical formula CP-1 is the following compound.

[0462]

[0463] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0464] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0465] Modes for Carrying Out the Invention

[0466] Below, in order to specifically describe the application, embodiments will be cited and described in detail. However, various forms can be deformed according to the embodiments of the application, and it is not interpreted that the scope of the application is limited to the embodiments described in detail below. The embodiments of the application are provided to more completely describe the application to those skilled in the art.

[0467] 1-1) Synthesis of Chemical Formula A1

[0468]

[0469] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0470] SM1 (1 equivalent) and SM2 (1.1 equivalents) were added to tetrahydrofuran (THF, excess), and then a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 2 mol%) was added, followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formula A1 (A1-1 to A1-8).

[0471] A1-1 to A1-8 of [Table A1] were synthesized by the same method except that SM1 and SM2 were changed in the synthesis method of the above-mentioned chemical formula A1.

[0472] [Table A1]

[0473]

[0474]

[0475] 1-2) Synthesis of Chemical Formula A2

[0476]

[0477] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0478] Under nitrogen conditions, compound A1 dissolved in tetrahydrofuran (excess) was dissolved, and after the compound was cooled to -78°C, 2.5M n-butyl lithium (n-BuLi) (1.2 equivalents) was added dropwise, and after stirring for 1 hour, iodine (1.1 equivalents) was added and stirred for 10 hours. After warming to room temperature (rt), 1N hydrogen chloride solution was added dropwise, and after extracting the organic layer, it was extracted with water twice. After removing the solvent, column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A2 (A2-1 to A2-8).

[0479] A2-1 to A2-8 of [Table A2] were synthesized by the same method except that SM1 and SM2 were changed in the synthesis method of the above-mentioned chemical formula A2.

[0480] [Table A2]

[0481]

[0482]

[0483] 1-3) Synthesis of Chemical Formula A3

[0484]

[0485] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0486] Compound A2 (1 equivalent), trimethylsilyl acetylene (TMS-≡, 5 equivalents), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.1 equivalent), copper iodide (CuI, 1 equivalent) and triethylamine (TEA, excess) were added, and heated and stirred at 70°C for 5 hours. After the reaction was completed, it was cooled to room temperature, passed through a filter filled with diatomaceous earth / silica gel, washed with chloroform, the solvent was removed, and column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A3 (A3-1 to A3-8).

[0487] A3-1 to A3-8 in [Table A3] were synthesized by the same method except that A2 was changed in the synthesis method of the above chemical formula A3.

[0488] [Table A3]

[0489]

[0490]

[0491] 1-4) Synthesis of Chemical Formula A4

[0492]

[0493] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0494] Compound A3 (1 equivalent) was dissolved in acetonitrile (AN, excess), silver fluoride (1.4 equivalent) was added, and after stirring for 30 minutes, N-iodosuccinimide (NIS, 1.4 equivalent) was added. The mixture was stirred at room temperature for 2 hours, and after confirming the completion of the reaction, it was filtered and washed with acetonitrile. The solvent was removed by vacuum distillation, and column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A4 (A4-1 to A4-8).

[0495] A4-1 to A4-8 of [Table A4] were synthesized by the same method except that A3 was changed in the synthesis method of the above chemical formula A4.

[0496] [Table A4]

[0497]

[0498]

[0499] 1-5) Synthesis of Chemical Formula A5

[0500]

[0501] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0502] Compound A4 (1 equivalent), platinum chloride (0.05 equivalent) and toluene (excess) were added, stirred at 100°C for 3 hours, and after confirming the completion of the reaction, cooled to room temperature. Filtered through a diatomaceous earth / silica gel pad, the solvent was removed by vacuum distillation, and column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A5 (A5-1 to A5-8).

[0503] A5-1 to A5-8 in [Table A5] were synthesized by the same method except that A4 was changed in the synthesis method of the above chemical formula A5.

[0504] [Table A5]

[0505]

[0506]

[0507] 1-6) Synthesis of Chemical Formula A6

[0508]

[0509] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0510] Compound A5 (1 equivalent) was dissolved in dichloromethane (excess), and then boron tribromide (BBr3, 1.4 equivalent) was added dropwise and stirred for 2 hours. After the reaction was completed, the reactant was added to water (excess), extracted, and further washed with water, and the solvent was removed by vacuum distillation, and hexane was added, stirred for 3 hours, and then filtered to produce the above-mentioned chemical formula A6 (A6-1 to A6-8).

[0511] A6-1 to A6-8 in [Table A6] were synthesized by the same method except that A5 was changed in the synthesis method of the above chemical formula A6.

[0512] [Table A6]

[0513]

[0514]

[0515] 1-7) Synthesis of Chemical Formula A7

[0516]

[0517] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0518] Compound A6 (1 equivalent) and potassium carbonate (2.5 equivalents) were added to N-methylpyrrolidone (NMP, excess), and the mixture was heated at 180°C and stirred for 3 hours. After confirming the completion of the reaction, it was cooled to room temperature, and water (excess, 2 times relative to the input solvent) was added and filtered, and the filtered solid was washed with water. Then, it was recrystallized with ethyl acetate and ethanol to produce the above chemical formula A7 (A7-1 to A7-8).

[0519] A7-1 to A7-8 in [Table A7] were synthesized by the same method except that A6 was changed in the synthesis method of the above-mentioned chemical formula A7.

[0520] [Table A7]

[0521]

[0522]

[0523] 1-8) Synthesis of Chemical Formula A8

[0524]

[0525] Here, ring A is a monocyclic or polycyclic hydrocarbon ring.

[0526] Compound A7 (1 equivalent) and SM3 (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (4,4,4',4'5,5,5'5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 1.3 equivalents) were added to 1,4-dioxaborolane. Potassium acetate (KOAc, 3 equivalents) was added to 1,4-dioxane (12 times the mass ratio of A7), stirred and refluxed. After stirring in oxane for 5 minutes, the mixture was added. After 2 hours, the reaction was confirmed to be complete and the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to produce the above chemical formula A8 (A8-1 to A8-8).

[0527] A8-1 to A8-8 in [Table A8] were synthesized by the same method except that A7 was changed in the synthesis method of the above chemical formula A8.

[0528] [Table A8]

[0529]

[0530]

[0531] 2-1) Synthesis of B1a

[0532]

[0533] Among them, R 101 To R 110 and X2 are the same as those in Formula 1, and X3 represents R in SM1 101 To R 104 Any one of is a halogen group, and in B1a, R 101 To R 110 Any one of is a halogen group, and R' is hydrogen or a leaving group.

[0534] SM1 (1 equivalent), SM2 (1.1 equivalent), palladium acetate (Pd(OAc)2, 0.05 equivalent), triphenylphosphine (PPh3, 0.2 equivalent) and cesium carbonate (Cs2CO3, 4 equivalent) were added to dimethylformamide (excess amount) and stirred at 140°C for 48 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate and water three times, and purified by silica gel column chromatography with ethyl acetate and hexane to produce the above-mentioned chemical formula B1a (B1a-1 to B1a-7).

[0535] B1a-1 to B1a-7 in [Table B1a] were synthesized by the same method except that SM1 and SM2 were changed in the synthesis method of the above chemical formula B1a.

[0536] [Table B1a]

[0537]

[0538]

[0539] 2-2) Synthesis of B1b

[0540]

[0541] Among them, R 101 To R 110 and X2 are the same as those in Formula 1, R' is hydrogen or a leaving group, and X3 represents R' and R in SM2 105 To R 110 Any one of is a halogen group, which represents R in B1b 101 To R 110 Any one of is a halogen group.

[0542] B1b (B1b-1 to B1b-5) were synthesized by the same method except that SM1 and SM2 in [Table B1b] were used in the synthesis method of the above chemical formula B1a.

[0543] [Table B1b]

[0544]

[0545] 2-3) Synthesis of B2

[0546]

[0547] SM1 (one of the chemical formulas B1a and B1b, 1 equivalent) and pinacol diboron (1.3 equivalents) were added to 1,4-dihydro- Potassium acetate (3 equivalents) was added to 1,4-dioxane (12 times the mass ratio of SM1), stirred and refluxed. Bis(diphenylphosphino)ferrocenepalladium dichloride (0.05 equivalents) was added to 1,4-dioxane. After stirring in oxane for 5 minutes, the mixture was added. After 2 hours, the reaction was confirmed to be complete and the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to produce the above chemical formula B2 (B2-1 to B2-11).

[0548] B2 (B2-1 to B2-11) were synthesized by the same method except that the synthesis method of the above chemical formula B2 was changed to SM1 in [Table B2].

[0549] [Table B2]

[0550]

[0551]

[0552] 3-1) Synthesis of Int.

[0553] wherein R101 to R110, X2, L1 and m are the same as those in Chemical Formula 1, Z1 and Z2 are different from each other and are each a halogen group, x is 1 or 2, and y is 1 or 2.

[0554] After SM1 (1 equivalent) and B2 (depending on the number of Z1, i.e., y, 1.1 equivalents or 2.1 equivalents) were added to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, tetrakis(triphenylphosphine)palladium (2 mol%) was added, and the mixture was heated and stirred at 85°C for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed with hexane and ethyl acetate to produce the above chemical formula int. (int1. to int12.).

[0555] In the synthesis method of the above chemical formula int., int. (int1. to int12.) was synthesized by the same method except that SM1 and B2 in [Table int.] were changed.

[0556] [table int.]

[0557]

[0558]

[0559] 3-2) Synthesis of Chemical Formula 1

[0560]

[0561] Wherein, R1 to R8, R101 to R110, X1, X2, L1 and m are the same as those in Chemical Formula 1, Z2 is a halogen group, x is 1 or 2, and y is 1 or 2.

[0562] After Int. (one of Int1. to Int12., 1 equivalent) and SM2 (depending on the number of Z2, ie, x, 1.1 equivalents or 2.1 equivalents) were added to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, tetrakis(triphenylphosphine)palladium (2 mol%) was added, and then heated and stirred at 85°C for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed with hexane and ethyl acetate to produce Chemical Formula 1 (Compounds 1 to 13).

[0563] Compounds 1-1 to 1-13 were synthesized by the same method except that SM1 and B2 in the synthesis method of the above chemical formula int. were respectively changed to Int. and SM2 in [Table 1H].

[0564] [Table 1H]

[0565]

[0566]

[0567]

[0568] 3-3) Synthesis of Chemical Formula 1D

[0569]

[0570] Chemical formula 1 (1 equivalent) and trifluoromethanesulfonic acid (catalyst (cat.)) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, and after stirring for 30 minutes, trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene and recrystallized to obtain Chemical Formula 1D (Compounds 1-14 to 1-17) in Table 1D below.

[0571] [Table 1D]

[0572]

[0573] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value determines the substitution rate.

[0574] Compounds 1-14 to 1-17 as the above products were synthesized with reference to existing documents of our company such as KR1790854B1.

[0575] [Production Example 2] Synthesis of Chemical Formula 2

[0576] 1) Synthesis of aromatic chemical formula 2

[0577]

[0578] Wherein, Ar3 is a substituted or unsubstituted aryl group.

[0579] The reactant (1 equivalent) and trifluoromethanesulfonic acid (TfOH, catalyst) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, stirred for 30 minutes, and trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene for recrystallization to obtain the product shown in [Table 2-1] below.

[0580] [Table 2-1]

[0581]

[0582]

[0583]

[0584]

[0585] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value determines the substitution rate.

[0586] Compounds A to W as the above-mentioned reactants were synthesized with reference to existing documents such as JP4070676B2, KR1477844B1, US6465115B2, JP3148176B2, JP4025136B2, JP4188082B2, JP5015459B2, KR1979037B1, KR1550351B1, KR1503766B1, KR0826364B1, KR0749631B1 and KR1115255B1. In addition, compounds 1-A to 1-W as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0587] 2) Synthesis of furan-based chemical formula 2

[0588]

[0589] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, stirred for 30 minutes, and trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene for recrystallization to obtain the products shown in [Table 2-2] to [Table 2-3] below.

[0590] [Table 2-2]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value determines the substitution rate.

[0597] Compounds 1# to 27# as the above-mentioned reactants were synthesized with reference to existing documents such as KR1964435B1, KR1899728B1, KR1975945B1, KR2018-0098122A, KR2018-0102937A and KR2018-0103352A. In addition, compounds 2-1 to 2-27 as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0598] [Table 2-3]

[0599]

[0600]

[0601]

[0602]

[0603] The degree of deuterium substitution of each product varies depending on the reaction time. + ) value determines the substitution rate.

[0604] Compounds 28# to 47# as the above-mentioned reactants were synthesized with reference to our company's existing documents such as KR1994238B1, KR1670193B1, KR1754445B1 and KR1368164B1. In addition, compounds 2-28 to 2-47 as deuterium-substituted products were synthesized with reference to the existing document KR1538534B1.

[0605] [Experimental Example 1] Dipole moment (DM) and sublimation temperature of manufacturing example 2

[0606] [Table 2-4]

[0607]

[0608]

[0609] At this time, the unit of dipole moment (DM) is debye, and the unit of sublimation temperature is °C.

[0610] The physical properties of the compounds synthesized in the above-mentioned preparation examples are shown in the above-mentioned [Table 2-4]. Regarding the physical properties of compounds A to W, although compounds 1-A to 1-W have chemical structural differences in carbon-hydrogen skeletons and carbon-deuterium skeletons, the basic chemical skeletons are the same, and the differences in dipole moments are almost the same, so the relevant numerical values ​​are collectively referred to as compounds A to W. In addition, compounds 1# to 47# are also the same as compounds 2-1 to 2-47, and the relevant numerical values ​​are collectively referred to as compounds 1# to 47#.

[0611] In the compound synthesized in the above-mentioned manufacturing example 2, the compound of the aryl-based chemical formula 2 (host 1) and the compound of the furan-based chemical formula 2 (host 2) have a difference in dipole moment in the chemical structure. Compounds A to W equivalent to the aryl-based chemical formula 2 have a skeleton based only on carbon and hydrogen by having an aryl-based substituent, and form a limited number of electrons in the chemical structure. The more and less partitions, the more the result of the dipole moment (DM) does not exceed 0.3 Debye. On the contrary, it can be confirmed that compounds 1# to 47# of the furan-based chemical formula 2 have a potential that can deepen the electronic partition in the chemical structure with a carbon-hydrogen skeleton by replacing the anthracene skeleton with a relatively electron-rich furan containing an aryl or heteroaryl group, and have a high dipole moment (DM) compared to compounds A to W of the aryl-based chemical formula. Therefore, the combination of the two structures suggested in this document has a range in which the difference in DM of the two hosts is at least greater than 0.2.

[0612] |DM 主体1 –DM 主体2 |>0.2

[0613] Furthermore, it was confirmed that the sublimation temperature of the compound synthesized in the above production example was lower than 400° C. If the sublimation temperature was higher than 400° C., there would be many limitations in the use as a material for an organic electroluminescent device.

[0614] Furthermore, in order to pre-sublimate a mixture of one of the aryl-based compounds of Chemical Formula 2 and one of the furan-based compounds of Chemical Formula 2, it is preferable that the following formula is satisfied.

[0615] |T sub1 –T sub2 |≤20℃

[0616] [Experimental Example 2] Preparation Example of Mixture

[0617] The premixability of two compounds (one compound each of Chemical Formula 2 and Chemical Formula 3) corresponding to the two main bodies to be mixed was tested by high pressure liquid chromatography (HPLC) analysis of the evaporated film. In the preparation example of this mixture, Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) were used.

[0618] For this purpose, 0.15 g of Compound J (or Compound 1-J) and 0.15 g of Compound 6# (or Compound 2-6) were mixed in a ratio of 1:1 and crushed. 0.3 g of the mixture was placed in the evaporation source of a VTE vacuum chamber. The chamber was evacuated to reduce the pressure to 10 -7 torr. In order to avoid cooling of the raw materials and keep them at an appropriate temperature, the evaporation process is not interrupted. After the film was formed, the substrate was replaced twice in succession. The evaporated film was analyzed by HPLC, and the results are shown below Figure 5 . Take 3 such substrate samples, represented by Film 1 to Film 3. The composition of Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) does not change significantly from Film 1 to Film 3. Through the entire process, the change in concentration before and after evaporation within 10%, preferably within 5%, is considered to be excellent and useful for commercial OLED applications, showing that the difference in sublimation temperature of the two mixed compounds can maintain the above-mentioned concentration change at a temperature difference of less than 20°C. The difference in sublimation temperature between the above-mentioned Compound J and Compound 6# is 10°C.

[0619] The slight variation in concentration shown below does not show any trend on the device. Sample collection and HPLC analysis can be explained by the following formula (2). More specifically, the first compound (Compound J) or the second compound (Compound 6#) has a concentration C1 in the above mixture. -4 Torr to 1×10 -9 In high vacuum evaporation equipment with a chamber base pressure of to The film formed by evaporating the mixture at a predetermined distance from the place where the mixture is evaporated has a concentration C2 and satisfies the following formula.

[0620] |(C1-C2) / C1|<10%

[0621] When the concentration C1 of the compound represented by compound 6# in the above composition is 48.85%, the concentration of membrane 1 is 47.69%, so the concentration change is 2.3%, the concentration of membrane 2 is 47.69%, so the concentration change is 3.9%, and the concentration of membrane 3 is 47.69%, so the concentration change is 2.3%.

[0622] The concentration change did not vary significantly in the prepared films 1 to 3, and it was observed that the variation between the films was small. Therefore, the above conditions are preferred.

[0623] [Experimental Example 3] Comparative Preparation Example of Mixture

[0624] The following are exemplary results of mixtures that deviate from the conditions presented in this specification. In the comparative preparation examples of the following mixtures, Compound B (Chemical Formula 2) and Compound 24# (Chemical Formula 3) were used.

[0625] For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 24# (or compound 2-24) were mixed in a ratio of 7:3 and crushed. The preparation conditions were the same as those of the mixture of the above-mentioned Preparation Example 3, and the results are shown below. Figure 6 .

[0626] According to the above formula 2, when the concentration C1 of the compound represented by compound B in the above composition is 69.30%, the concentration of membrane 1 is 65.42%, so the concentration change is 5.5%, the concentration of membrane 2 is 61.22%, so the concentration change is 11.6%, and the concentration of membrane 3 is 62.82%, so the concentration change is 9.3%.

[0627] In the films 1 to 3 produced, the concentration changes significantly varied, and in particular, a change of 10% or more was observed, and it was observed that there was a large variation between the films. Therefore, the above conditions are not preferred.

[0628] [Experimental Example 4] Fabrication of OLED

[0629] <Example 1>

[0630] The ITO / Ag / ITO as anode is The substrate to be deposited was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0631] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, as the first light-emitting layer, the host compound 1-1 synthesized in Preparation Example 1 and the dopant BD1 (2 wt%) were mixed in an amount of 1:1. Then, as the second light-emitting layer, the host compound A of Preparation Example 2 and the dopant BD1 (2 wt %) were mixed in an amount of Then, HB1 was deposited by vacuum evaporation to form a light-emitting layer. To form an electron regulating layer, the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer of The thickness of magnesium and lithium fluoride (LiF) film is used as the electron injection layer <eil>Then, as the cathode, magnesium and silver (1:4) were used to form After that, CP1 was evaporated Thus, the device is completed. In the above process, the evaporation rate of the organic matter is maintained at

[0632] <Comparative Examples 1 to 8 and Examples 2 to 86>

[0633] In the above Comparative Examples 1 to 8 and Examples 2 to 86, devices were manufactured by the same method as in Example 1, except that the substances described in the following [Table 1] were used as materials for the light-emitting layer.

[0634] For the devices manufactured in Comparative Examples 1 to 8 and Examples 1 to 86, the 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of . The results are shown in the following [Table 1].

[0635] [Table 1]

[0636]

[0637]

[0638]

[0639]

[0640]

[0641]

[0642] The results of [Table 1] above are the case where the device structure is formed of two light-emitting layers, the main body of the first light-emitting layer and the main body of the second light-emitting layer are single main bodies of each layer, and the compound of Chemical Formula 1 constitutes the main body of the first light-emitting layer. Comparative Examples 1 to 4 use an aryl series anthracene main body as the main body of the second light-emitting layer, and show low efficiency and life, especially significantly high voltage compared with Examples 1 to 86. Among them, it can be seen that Comparative Examples 2 and 3 are structures in which the main body of the second light-emitting layer contains deuterium. Even if there is a certain degree of life improvement effect, it is significantly lower than the embodiment, and the overall device performance effect is not large. In addition, in Comparative Example 4, where BD2 as a boron-based blue dopant is applied, the trend of Comparative Example 2 is also maintained.

[0643] Comparative Examples 5 to 8 use furan anthracene as the main body of the second light-emitting layer, which also shows low voltage compared with Comparative Examples 1 to 4, but also shows low efficiency and life, and high voltage compared with Examples 1 to 86. Among them, it can be seen that Comparative Example 7 is a structure in which the main body of the second light-emitting layer contains deuterium, just like Comparative Examples 2 and 3 above. Even if there is a certain degree of life improvement effect, it is significantly lower than that of the examples, and the overall device performance effect is not great. In addition, in Comparative Example 8, where BD2 as a boron-based blue dopant is applied, the trend when compared with Comparative Example 7 is also maintained.

[0644] In Examples 1 to 86 of the present application, it can be seen that the compound equivalent to Chemical Formula 1 is used as the main body of the first light-emitting layer, which plays a role in increasing the injection of holes and the potential barrier of electrons, and changing the light-emitting area within the light-emitting layer. As the main body of the second light-emitting layer, an anthracene main body substituted with an existing aromatic or furan series is used to maintain the low voltage characteristics and efficiency currently considered important in blue light-emitting devices, while ensuring the performance of the device.

[0645] In Examples 1 to 23, the compound of Chemical Formula 1 was used as the host of the first light-emitting layer, and the aryl anthracene host was used as the host of the second light-emitting layer. The case where the H compound not applied to deuterium was introduced as the host of the second light-emitting layer (Examples 1, 5, 8, 12, 16 and 21) and the case where the D compound applied to deuterium was introduced (the rest other than the above) were evaluated, and the effect of the two light-emitting layers was confirmed in each case. Data that the lifetime can be further improved by deuterium substitution of the host of the second light-emitting layer was seen, and it was confirmed that the device performance of the case where the compound of Chemical Formula 1 was used as the host of the first light-emitting layer was indeed improved.

[0646] In this regard, in Examples 24 to 27, the compound of Chemical Formula 1 was deuterated and used as a host of the first light-emitting layer to compare device results compared with Examples 1, 4, 14 and 3. It can be observed that the first light-emitting layer formed adjacent to the hole regulating layer further improves life by deuterium substitution.

[0647] In Examples 28 to 31, only the blue dopant in the devices of Examples 24 to 27 was changed from BD1 to BD2, and the trend and performance of the device were confirmed. When the boron-based dopant BD2 was used, it was confirmed that the efficiency was further improved while the trend of improving the life was maintained.

[0648] Embodiments 32 to 58 are different from Embodiments 1 to 23 in that anthracene derivatives combined with various heteroaromatic groups such as dibenzofuran, naphthylbenzofuran, and triphenyldifuran are introduced as the main body of the second light-emitting layer. Although they show characteristics of relatively low voltage and low lifetime compared to Embodiments 1 to 23, in the device structure manufactured by using the compound of Chemical Formula 1 as the main body of the first light-emitting layer, it can be confirmed that the device is improved while maintaining the characteristics as in the above-mentioned Embodiments 1 to 23.

[0649] In Examples 79 to 86, changes were introduced as in Examples 24 to 31, and the results were also verified to be excellent device performance.

[0650] <Example 87> Production of OLED

[0651] The ITO / Ag / ITO as anode is The deposited substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water with a dispersant dissolved therein, and washed with ultrasound. The detergent used was a product of Fisher, and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvents and dried.

[0652] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, as the first light-emitting layer, the host compound 1-12 synthesized in Preparation Example 1 and the dopant BD1 (2 wt %) were mixed in an amount of 1:1 to 2:1. Then, as the second light-emitting layer, the host compound B of Preparation Example 2, the compound 2-3 of Preparation Example 2 and the dopant BD1 (2 wt %) were mixed in an amount of 100 wt % and 200 wt %. Then, HB1 was evaporated to form a light-emitting layer. To form an electron regulating layer, the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer of The thickness of magnesium and lithium fluoride (LiF) film is used as the electron injection layer <eil>Then, as the cathode, magnesium and silver (1:4) were used to form After that, CP1 was evaporated In the above process, the evaporation rate of organic matter is maintained at

[0653]

[0654] [Comparative Examples 9 to 18 and Examples 88 to 122]

[0655] In the above-mentioned Comparative Examples 9 to 18 and Examples 88 to 122, devices were manufactured by the same method as that of the above-mentioned Example 87, except that the substances described in the following Table 2 were used as materials for the light-emitting layer.

[0656] However, as shown in [Table 2], the host of the second light-emitting layer shows both an example in which two hosts are co-evaporated from different evaporation sources during device manufacturing to form the light-emitting layer and an example in which a premix of two host compounds is used.

[0657] In particular, the conditions for preparing the host of the second light-emitting layer as a premix are as described above, and the two hosts of the second light-emitting layer used in Comparative Examples 9 to 18 and Examples 87 to 122 in [Table 2] can all be prepared as a premix as shown in [Table 3] below.

[0658] The devices prepared in Comparative Examples 9 to 18 and Examples 87 to 122 were heated at 20 mA / cm 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of . The results are shown in the following [Table 2].

[0659] [Table 2]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665] [Table 3]

[0666]

[0667]

[0668] The results of [Table 2] above indicate that the light-emitting layer is formed of two layers, the main body of the first light-emitting layer is the compound of Chemical Formula 1 as a single main body, and the main body of the second light-emitting layer is composed of two anthracene mixed main bodies co-evaporated or pre-mixed as a mixed main body. Comparative Examples 9 and 10 are examples of using H compounds (skeletons substituted with only hydrogen) and D compounds (compounds partially or completely substituted with deuterium) among widely used aryl anthracene compounds to prepare co-evaporation or premix and evaporate to form the main body of the second light-emitting layer. Furthermore, Comparative Examples 11, 12, and 13 are examples of preparing two kinds of aryl anthracene compounds and heteroaryl anthracene compounds (one or more of the two is the D compound) as co-evaporation or premix and evaporate to form the main body of the second light-emitting layer. Comparative Examples 14, 15, and 16 are examples of preparing two kinds of heteroaryl anthracene compounds (one or more of the two is the D compound) as co-evaporation or premix and evaporate to form the main body of the second light-emitting layer.

[0669] Compared with the single host case of Comparative Examples 1 to 8 in [Table 1] above, it can be seen that the device performance is improved by using a mixed host to form the light-emitting layer. In addition, Comparative Examples 17 and 18, like Comparative Example 4 in [Table 1], used a boron-based blue dopant, and it can be confirmed that the characteristics are maintained and the device performance is improved in the case of a mixed host (co-evaporation or premix production).

[0670] In Examples 87 to 102, the compound of Chemical Formula 1 is used as the main body of the first light-emitting layer, and the main body of the second light-emitting layer is formed by co-evaporation (1:1 weight ratio) of a combination of various anthracene (aryl or heteroaryl series, one of the two is a D compound substituted by deuterium) compounds, thereby showing very excellent voltage and efficiency characteristics compared with Comparative Examples 9 to 18, and the lifespan can also be improved.

[0671] In Examples 103 to 106, the host of the second light-emitting layer is different from that of Examples 87 to 102, and the device is made by co-evaporation of D compounds in which two hosts are both substituted with deuterium, and the average life span is increased by 10% compared with Examples 89, 88, 100 and 87. In Examples 107 to 110, the device is formed by using compounds 1-14 to 1-17 in which deuterated compounds 1-1, 1-6, 1-11 and 1-12 in the compound of Chemical Formula 1 are applied to the first light-emitting layer. As mentioned in the results of [Table 1], in the case of the first light-emitting layer formed adjacent to the hole regulating layer, further improvement in life span can be observed by deuterium substitution.

[0672] Examples 111 to 114 are devices manufactured by changing the host co-evaporation method of the second light-emitting layer of Examples 107 to 110 to a method of forming a premix of two hosts and then evaporating them in one evaporation source. The formation conditions of the premix are implemented with reference to the above description, and due to the uniform mixing effect of molecular units, the device performance of the co-evaporation device is maintained or stably improved.

[0673] Examples 115 to 118 are cases where BD2 (boron-based blue dopant) is applied to one or both of the two light-emitting layers and a premixed main body is applied. It can be seen that compared with the pyrene dopant, high efficiency is maintained while also maintaining the advantages of the premixed main body.

[0674] Examples 119 to 122 are situations in which the ratio of the two compounds in the premix of the second light-emitting layer in Examples 115 to 118 is changed and then produced and evaporated to form a main body, showing that the advantages and disadvantages of the two compounds can be reflected in the device by adjusting the ratio.< / eil> < / eil>

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X1 and X2 are the same or different from each other and are each independently O or S, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, in, L1 is further substituted or unsubstituted by deuterium, hydroxyl, cyano, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and optionally, at least one of the substituents of L1 may be combined with an adjacent substituent to form one or more substituted or unsubstituted rings, One of R1 to R8 and R 101 To R 110 One of them is connected to L1, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, and may be combined with adjacent substituents to form a substituted or unsubstituted ring, m is an integer of 1 to 4. When m is 2 or more, L1 are the same or different from each other. x is 1 or 2, y is 1 or 2, When x and y are each 2, the structures in the brackets are the same as or different from each other.

2. The compound according to claim 1, wherein The x is 1, the y is 1, or The x is 1, the y is 2, or The x is 2, and the y is 1.

3. The compound according to claim 1, wherein The x is 1, the y is 1, and the L1 is the following chemical formula A or B: [Chemical formula A] [Chemical formula B] In the chemical formulas A and B, X1 and X2 are the same or different from each other and are each independently O or S, Two of R1 to R8 and R 101 To R 110 Two of them are each connected to an adjacent group, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may optionally be combined with adjacent substituents to form a substituted or unsubstituted ring, * indicates the binding position.

4. The compound according to claim 1, wherein The x is 1, the y is 1, the R1 to R8 and R 101 To R 110 One of the following chemical formulas A-1 or B-1: [Chemical formula A-1] [Chemical formula B-1] In the chemical formulas A-1 and B-1, X1 and X2 are the same or different from each other and are each independently O or S, Two of R1 to R8 and R 101 To R 110 Two of them are each connected to an adjacent group, and the others are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, cyano, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and may optionally be combined with adjacent substituents to form a substituted or unsubstituted ring, * indicates the binding position.

5. The compound according to claim 1, wherein R1 and R2, R2 and R3, and R4 and R5, R 101 With R 102 , R 102 With R 103 , R 103 With R 104 , R 105 With R 106 , R 106 With R 107 , R 108 With R 109 , and R 109 With R 110 At least one of them is combined to form a substituted or unsubstituted hydrocarbon ring.

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

7. An organic light-emitting device, comprising: An anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers comprises the compound of Chemical Formula 1 according to any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein: The organic layer includes a light-emitting layer disposed between the anode and the cathode, The light-emitting layer includes a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer. The first light emitting layer includes the compound of Chemical Formula 1.

9. The organic light emitting device according to claim 8, wherein: The second light-emitting layer includes at least one of the following compounds of Chemical Formula 2 and Chemical Formula 3: [Chemical formula 2] In the chemical formula 2, At least one of R11 to R20 is bonded to the * site of the following chemical formula 2-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, [Chemical formula 2-1] In the chemical formula 2-1, L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar2 is a substituted or unsubstituted aryl group, p is an integer from 1 to 3, [Chemical formula 3] In the chemical formula 3, At least one of Y1 to Y10 is bonded to the * site of the following chemical formula 3-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, [Chemical formula 3-1] In the chemical formula 3-1, A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle, L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, q is an integer from 1 to 3.

10. The organic light emitting device according to claim 9, wherein: The first light-emitting layer of the light-emitting layer comprises the compound of Chemical Formula 1 as a first host material, The second light emitting layer includes at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 as a second host material.

11. The organic light emitting device according to claim 8, wherein: The first light-emitting layer and the second light-emitting layer each further include a dopant substance.

12. The organic light emitting device according to claim 11, wherein: The dopant substance is a fluorescent dopant.

13. The organic light emitting device according to claim 12, wherein: The fluorescent dopant is a pyrene compound or a non-pyrene compound.

14. The organic light emitting device according to claim 13, wherein: The non-pyrene compound is an arylamine compound or a boron compound.

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