Heterocyclic compounds and organic light-emitting devices containing them

Abstract

This specification aims to provide heterocyclic compounds and organic light-emitting devices containing them. [Solution] This specification relates to a heterocyclic compound of chemical formula 1 and an organic light-emitting element containing the same.

Description

[Technical Field]

[0001] This application claims the benefit as of the filing date of Korean Patent Application No. 10-2024-0122364, filed with the Korean Intellectual Property Office on September 9, 2024, and all its contents are incorporated herein by reference. This specification relates to heterocyclic compounds and organic light-emitting devices containing them. [Background technology]

[0002] Electroluminescent elements are a type of self-emissive display element that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0003] An organic light-emitting device has a structure in which an organic thin film is placed between two electrodes. When a voltage is applied to such an organic light-emitting device, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, which then annihilate each other, emitting light. The organic thin film can be composed of a single layer or multiple layers, as needed.

[0004] The material for the organic thin film can have a light-emitting function as needed. For example, the organic thin film material may be a compound that can constitute a light-emitting layer on its own, or a compound that can play the role of a host or dopant in a host-dopant light-emitting layer. In addition, the organic thin film material may be a compound that can perform roles such as hole injection, hole transport, electron blockade, hole blockade, electron transport, and electron injection.

[0005] To improve the performance, lifespan, or efficiency of organic light-emitting devices, there is a continuous need for the development of organic thin-film materials. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] U.S. Patent No. 4,356,429 [Overview of the project] [Problems that the invention aims to solve]

[0007] This specification aims to provide heterocyclic compounds and organic light-emitting devices containing them. [Means for solving the problem]

[0008] In one embodiment of this specification, a heterocyclic compound of the following chemical formula 1 is provided. [ka]

[0009] In the aforementioned chemical formula 1, M is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group. Ar is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. R1 to R3 are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; or substituted or unsubstituted C2 to C60 heterocycloalkyl group. R4 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. o is an integer from 0 to 5, and if o is 2 or greater, R4 may be the same or different. Het is a group represented by one of the following chemical formulas H-1 to H-3:

Chem.

[0010] In the above chemical formulas H-1 to H-3, Z is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, m is an integer from 0 to 4. When m is 2 or more, Z may be the same as or different from each other, R5 and R6 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, p is an integer from 1 to 3, q is an integer from 1 to 5. When p and q are each 2 or more, R5 and R6 may be the same as or different from each other.

[0011] In another embodiment of the present specification, an organic light-emitting device includes a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers provides an organic light-emitting device containing one or more of the above compounds.

Advantages of the Invention

[0012] The heterocyclic compound described in the present specification can lower the driving voltage of the device, improve the light-emitting efficiency, and improve the lifetime characteristics of the device when used in an organic light-emitting device.

[0013] Specifically, it contains phenanthroline having a substituent at a specific position as the first substituent around the benzene ring, and contains a linking group of pyridine and quinoline as the second substituent. The first substituent and the second substituent are substituted at the meta position on the benzene ring. When substituted at the meta position in this way, the binding energy with the metal (Li or Yb) doped while the amine of quinoline or pyridine strongly coordinates with the metal becomes high.

[0014] In addition, the linking group of pyridine and quinoline as the second substituent is bonded to the benzene ring only at a specific position, and the linking structure between pyridine and quinoline is also specified. When pyridine / quinoline is linked to quinoline / pyridine substituted at the meta position in this way, the amine of pyridine / quinoline can further bind to the metal, and a stronger bond can be formed. As a result, excellent effects in terms of driving voltage and efficiency can be obtained.

[0015] The heterocyclic compound including the structural features has appropriate electron transport ability, is structurally stable, and can efficiently transfer electrons. Therefore, when the heterocyclic compound of the present invention is used as a material for the organic layer (especially the electron transport layer and the charge generation layer) of an organic light-emitting device, the performance of the organic light-emitting device can be improved.

Brief Description of the Drawings

[0016] <00001​​​​​​​​​​​​​​​​​​The following provides a more detailed description of this specification.

[0018] In this specification, when a part "includes" a component, this means that, unless otherwise stated, it may include other components rather than excluding them.

[0019] In this specification, "N~N'" means N or greater and N' or less.

[0020] In this specification, Cn (n: an integer greater than or equal to 1) means the number of carbon atoms. For example, C1 to C60 means carbon atoms numbering from 1 to 60.

[0021] In this specification, the chemical formula [ka] or [ka] This indicates the position where they are joined.

[0022] The term "substitution" means that a hydrogen atom bonded to a carbon or nitrogen atom of a compound is replaced by another substituent. The position of substitution is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted. If two or more substituents are substituted, the two or more substituents may be the same or different.

[0023] In this specification, "substituted or unsubstituted" means that a molecule is substituted with at least one substituent selected from the group consisting of deuterium; halogen groups; cyano groups (-CN); C1-C60 alkyl groups; C2-C60 alkenyl groups; C2-C60 alkynyl groups; C1-C60 haloalkyl groups; C1-C60 alkoxy groups; C6-C60 aryloxy groups; C1-C60 alkylthiooxy groups; C6-C60 arylthiooxy groups; C1-C60 alkylsulfoxy groups; C6-C60 arylsulfoxy groups; C3-C60 cycloalkyl groups; C2-C60 heterocycloalkyl groups; C6-C60 aryl groups; C2-C60 heteroaryl groups; silyl groups; phosphine oxide groups; and amine groups, or is substituted with a substituent in which at least two substituents selected from the above substituents are linked, or is unsubstituted.

[0024] In this specification, "where no substituents are shown in the chemical formula or structure of a compound," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 Since H (deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0025] In one embodiment of this application, "when no substituents are shown in the chemical formula or structure of the compound" can mean that all positions that could have substituents are either hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some of the hydrogen atoms may be deuterium, which is an isotope. In this case, the deuterium content may be 0% to 100%, and the deuterium content can also be expressed as a deuterium substitution rate.

[0026] In one embodiment of this application, when "substituents are not represented in the chemical formula or structure of the compound," and when deuterium is not explicitly excluded, such as "deuterium content is 0%, hydrogen content is 100%" or "all substituents are hydrogen," hydrogen and deuterium can be used together in the compound.

[0027] In one embodiment of this application, deuterium is an isotope of hydrogen, having a deuteron as its nucleus, which consists of one proton and one neutron, and can be represented as hydrogen-2, with the element symbol D or 2 It can be written as H.

[0028] In one embodiment of this application, isotope elements refer to atoms that have the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0029] In one embodiment of this application, the meaning of the substitution rate T% of a particular substituent can be defined as T2 / T1X100 = T% when T1 is defined as the total number of substituents that the basic compound may have, and T2 is defined as the number of specific substituents among them.

[0030] In other words, in one example, [ka] A phenyl group represented by can be expressed as having a deuterium substitution rate of 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and of these, the number of deuterium atoms is 1 (T2 in the formula). In other words, a phenyl group with a deuterium substitution rate of 20% can be represented by the following structural formula. [ka]

[0031] Furthermore, in one embodiment of this application, the term "phenyl group with a deuterium substitution rate of 0%" can mean a phenyl group that does not contain a deuterium atom as a substituent, i.e., a phenyl group having five hydrogen atoms.

[0032] In this specification, halogen may be fluorine, chlorine, bromine, or iodine.

[0033] In this specification, alkyl groups include linear or branched chains having 1 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, more specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, Examples include, but are not limited to, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0034] In this specification, the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, more specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, and styrenyl group.

[0035] In this specification, the alkynyl group includes a linear or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, more specifically 2 to 40, and more specifically 2 to 20.

[0036] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3 and -CF2CF3.

[0037] In this specification, an alkoxy group is represented by -O(R101), where R101 can be one of the alkyl groups exemplified above.

[0038] In this specification, an aryloxy group is represented by -O(R102), where R102 can be the example of the aryl group described above.

[0039] In this specification, the alkylthiooxy group is represented by -S(R103), where R103 can be represented by the examples of alkyl groups described above.

[0040] In this specification, the aryl thioxy group is represented by -S(R104), and R104 can be the example of the aryl group described above.

[0041] In this specification, an alkyl sulfoxy group is represented by -S(=0)2(R105), where R105 can be an example of the alkyl group described above.

[0042] In this specification, the aryl sulfoxy group is represented as -S(=0)2(R106), and R106 can be represented by the aforementioned aryl group example.

[0043] In this specification, cycloalkyl groups include monocyclic or polycyclic groups having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly linked or fused with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be other types of ring groups, such as heterocycloalkyl groups, aryl groups, heteroaryl groups, etc. The number of carbon atoms in the cycloalkyl group may be 3 to 60, more specifically 3 to 40, and more specifically 5 to 20. Specifically, examples include, but are not limited to, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, 3-methylcyclopentyl groups, 2,3-dimethylcyclopentyl groups, cyclohexyl groups, 3-methylcyclohexyl groups, 4-methylcyclohexyl groups, 2,3-dimethylcyclohexyl groups, 3,4,5-trimethylcyclohexyl groups, 4-tert-butylcyclohexyl groups, cycloheptyl groups, and cyclooctyl groups.

[0044] In this specification, a heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly linked or fused with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be other types of ring groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, more specifically 2 to 40, and more specifically 3 to 20.

[0045] In this specification, the aryl group includes a monocyclic or polycyclic group having 6 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which the aryl group is directly linked or fused with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, more specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, crisenyl group, phenantrenyl group, perilenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthyleneyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0046] In this specification, the terphenyl group can be selected from the following structures. [ka]

[0047] In this specification, the fluorenyl group may be substituted, and adjacent substituents may bond to each other to form a ring. That is, substituted or unsubstituted fluorenyl groups may also include spirobifluorenyl groups.

[0048] When the fluorenyl group is substituted, for example, the following structure can be obtained, and any carbon in the following structure may be bonded to another structure, but is not limited to this. [ka]

[0049] In this specification, a heteroaryl group comprises S, O, Se, N, or Si as a heteroatom, and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted by other substituents. Here, polycyclic means a group in which the heteroaryl group is directly linked or fused with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, more specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include pyridine group, pyrrole group, pyrimidine group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, triazole group, furazan group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxin group, triazine group, tetrazine group, and k Noline group, isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthoridine group, imidazopyridine group, diazanaphthalene group, triazaidene group, indole group, indidine group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phena Zin group, dibenzosilole group, spirovi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indro[2,3-a]carbazole group, indro[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothio Examples of such groups include, but are not limited to, the fen group, benzo[c][1,2,5]thiadiazole group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indoline group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0050] In this specification, the benzocarbazole group may be any of the following structures, in which nitrogen or any carbon is bonded to another structure. If any carbon is bonded to another structure, nitrogen is bonded to hydrogen or has an additional substituent. [ka]

[0051] In this specification, the dibenzocarbazole group may be any of the following structures, in which nitrogen or any carbon is bonded to another structure. If any carbon is bonded to another structure, nitrogen is bonded to hydrogen or has an additional substituent. [ka]

[0052] In this specification, when a substituent is a carbazole group, a benzocarbazole group, or a dibenzocarbazole group, it means that the nitrogen or carbon of the carbazole group, benzocarbazole group, or dibenzocarbazole group is bonded to another structure.

[0053] In this specification, when a carbazole group, benzocarbazole group, or dibenzocarbazole group is substituted, it means that an additional substituent is substituted on the nitrogen or carbon of the carbazole group, benzocarbazole group, or dibenzocarbazole group.

[0054] In this specification, the naphthobenzofuran group may have any of the following structures, and any carbon in any of the following structures may be bonded to another structure. [ka]

[0055] In this specification, the naphthobenzothiophene group may have any of the following structures, and any carbon in any of the following structures may be bonded to another structure. [ka]

[0056] In this specification, the silyl group is a substituent comprising Si, wherein the Si atom is directly linked as a radical, and is represented as -Si(R107)(R108)(R109), where R107 to R109 may be identical or different from each other and each independently consist of at least one of the following substituents: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0057] The silyl group may include alkylsilyl groups, arylsilyl groups, heteroarylsilyl groups, alkylarylsilyl groups, arylheteroarylsilyl groups, etc., depending on the substituent bonded to the Si element. An alkylsilyl group, arylsilyl group, or heteroarylsilyl group means that the Si element of the silyl group is substituted with an alkyl group, an aryl group, or a heteroaryl group, respectively. An alkylarylsilyl group means that the Si element of the silyl group is substituted with an alkyl group and an aryl group, and an arylheteroarylsilyl group means that the Si element of the silyl group is substituted with an aryl group and a heteroaryl group.

[0058] In this specification, a triarylsilyl group means a silyl group substituted with three aryl groups. The number of carbon atoms in the aryl groups may be 6 to 60, 6 to 30, or 6 to 20, and the number of carbon atoms in the triarylsilyl group may be 18 to 180, 18 to 90, or 18 to 60.

[0059] The following structures are examples of silyl groups, but are not limited to these. [ka]

[0060] In this specification, a phosphine oxide group is represented as -P(=O)(R110)(R111), where R110 and R111 are identical or different, and each may independently be a substituent consisting of at least one of the following: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group described above can be applied. For example, phosphine oxide groups include, but are not limited to, dimethylphosphine oxide, diphenylphosphine oxide, and dinaphthylphosphine oxide.

[0061] In this specification, an amine group is represented as -N(R112)(R113), where R112 and R113 are identical or different, and each may independently be a substituent consisting of at least one of hydrogen, deuterium, halogen group, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group. The amine group can be selected from the group consisting of -NH2, monoalkylamine group, monoarylamine group, monoheteroarylamine group, dialkylamine group, diarylamine group, diheteroarylamine group, alkylarylamine group, alkylheteroarylamine group, and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorenylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group.

[0062] In this specification, the above description of aryl groups can be applied, except that the arylene group is a divalent group.

[0063] In this specification, the above description of heteroaryl groups can be applied, except that the heteroarylene group is a divalent group.

[0064] One embodiment of this specification provides a heterocyclic compound of the following chemical formula 1. [ka]

[0065] In the aforementioned chemical formula 1, The definitions of each substituent are as described above.

[0066] A heterocyclic compound according to one embodiment of this specification is characterized in that it comprises a benzene ring, a phenanthroline having a substituent at a specific position as a first substituent, and a pyridine-quinoline linking group as a second substituent, wherein the first substituent and the second substituent are substituted at the meta position on the benzene ring.

[0067] In the heterocyclic compound with the aforementioned structure, the quinoline and pyridine amines strongly coordinate with the metal, resulting in high bonding energy with the doped metal (Li or Yb). Consequently, excellent effects in terms of driving voltage and efficiency can be obtained. Furthermore, it possesses suitable electron transport capabilities, is structurally stable, and can efficiently transfer electrons.

[0068] In one embodiment of this specification, the chemical formula 1 can be represented by any of the following chemical formulas 1-1 to 1-3. [ka] [ka]

[0069] In the above chemical formulas 1-1 to 1-3, The definitions of each substituent are the same as those in Chemical Formula 1 above.

[0070] In one embodiment of this specification, the chemical formula 1 can be represented by the following chemical formulas 1-1-1, 1-1-2, 1-2-1, or 1-3-1. [ka] [ka]

[0071] In the aforementioned chemical formulas 1-1-1, 1-1-2, 1-2-1, and 1-3-1, The definitions of each substituent are the same as those in Chemical Formula 1 above.

[0072] In one embodiment of this specification, the chemical formula 1-3-1 can be represented by the following chemical formulas 1-3-A or 1-3-B. [ka]

[0073] In the above chemical formulas 1-3-A and 1-3-B, The definitions of each substituent are the same as those in Chemical Formula 1 above.

[0074] In one embodiment of this specification, M is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0075] In one embodiment of this specification, M may be a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0076] In one embodiment of this specification, M may be a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0077] In one embodiment of this specification, M may be a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0078] In one embodiment of this specification, M may be a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N.

[0079] In one embodiment of this specification, M may be a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing a C=N bond.

[0080] In one embodiment of this specification, M may be a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridine group.

[0081] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted C1-C40 alkyl group; a deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted C6-C40 aryl group; or a deuterium-substituted or unsubstituted C2-C40 heteroaryl group.

[0082] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted C1-C20 alkyl group; a deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted C6-C20 aryl group; or a deuterium-substituted or unsubstituted C2-C20 heteroaryl group.

[0083] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted C1-C10 alkyl group; a deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted C6-C20 aryl group; or a deuterium-substituted or unsubstituted C2-C20 heteroaryl group.

[0084] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted C1-C10 alkyl group; a deuterium-substituted or unsubstituted C6-C20 aryl group; or a deuterium-substituted or unsubstituted C2-C20 heteroaryl group containing N.

[0085] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted C1-C10 alkyl group; a deuterium-substituted or unsubstituted C6-C20 aryl group; or a deuterium-substituted or unsubstituted C2-C20 heteroaryl group containing a C=N bond.

[0086] In one embodiment of this specification, M may be a deuterium-substituted or unsubstituted tert-butyl group; a deuterium-substituted or unsubstituted phenyl group with a deuterium, a tert-butyl group, or a deuterium-substituted tert-butyl group; or a deuterium-substituted or unsubstituted pyridine group.

[0087] In one embodiment of this specification, Ar is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group.

[0088] In one embodiment of this specification, Ar may be hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C40 alkyl group; substituted or unsubstituted C6-C40 aryl group; or substituted or unsubstituted C2-C40 heteroaryl group.

[0089] In one embodiment of this specification, Ar may be hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heteroaryl group.

[0090] In one embodiment of this specification, Ar may be hydrogen; deuterium; substituted or unsubstituted C1-C10 alkyl groups; substituted or unsubstituted C6-C20 aryl groups; or substituted or unsubstituted C2-C20 heteroaryl groups.

[0091] In one embodiment of this specification, Ar may be hydrogen; deuterium; substituted or unsubstituted C1-C10 alkyl groups; substituted or unsubstituted C6-C20 aryl groups; or substituted or unsubstituted C2-C20 heteroaryl groups containing O or S.

[0092] In one embodiment of this specification, Ar may be hydrogen; deuterium; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted benzofuran group; or a substituted or unsubstituted benzothiophene group.

[0093] In one embodiment of this specification, Ar may be hydrogen; deuterium; halogen group; cyano group; deuterium-substituted or unsubstituted C1-C40 alkyl group; deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted C6-C40 aryl group; or deuterium-substituted or unsubstituted C2-C40 heteroaryl group.

[0094] In one embodiment of this specification, Ar may be hydrogen; deuterium; halogen group; cyano group; deuterium-substituted or unsubstituted C1-C20 alkyl group; deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted C6-C20 aryl group; or deuterium-substituted or unsubstituted C2-C20 heteroaryl group.

[0095] In one embodiment of this specification, Ar may be hydrogen; deuterium; deuterium-substituted or unsubstituted C1-C10 alkyl groups; deuterium, alkyl groups, or deuterium-substituted alkyl groups, or unsubstituted C6-C20 aryl groups; or C2-C20 heteroaryl groups.

[0096] In one embodiment of this specification, Ar may be hydrogen; deuterium; deuterium-substituted or unsubstituted C1-C10 alkyl groups; deuterium, alkyl groups, or deuterium-substituted alkyl groups, or unsubstituted C6-C20 aryl groups; or C2-C20 heteroaryl groups containing O or S.

[0097] In one embodiment of this specification, Ar may be hydrogen; deuterium; a deuterium-substituted or unsubstituted tert-butyl group; a deuterium, alkyl group, or deuterium-substituted alkyl group substituted or unsubstituted phenyl group; a benzofuran group; or a benzothiophene group.

[0098] In one embodiment of this specification, Ar may be hydrogen; deuterium; a deuterium-substituted or unsubstituted tert-butyl group; a deuterium-substituted, tert-butyl group, or deuterium-substituted tert-butyl group, or an unsubstituted phenyl group; a benzofuran group; or a benzothiophene group.

[0099] In one embodiment of this specification, R1 to R3 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group.

[0100] In one embodiment of this specification, R1 to R3 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; or a substituted or unsubstituted C2 to C40 heterocycloalkyl group.

[0101] In one embodiment of this specification, R1 to R3 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; or a substituted or unsubstituted C2-C20 heterocycloalkyl group.

[0102] In one embodiment of this specification, R1 to R3 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C1 to C20 alkyl group.

[0103] In one embodiment of this specification, R1 to R3 may each be independently hydrogen or deuterium.

[0104] In one embodiment of this specification, R1 to R3 may be hydrogen.

[0105] In one embodiment of this specification, R4 may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; or a substituted or unsubstituted C2-C60 heterocycloalkyl group.

[0106] In one embodiment of this specification, R4 may be hydrogen; deuterium; a halogen group; a cyano group; or a substituted or unsubstituted C1-C60 alkyl group.

[0107] In one embodiment of this specification, R4 may be hydrogen; or deuterium.

[0108] In one embodiment of this specification, R4 may be hydrogen.

[0109] In one embodiment of this specification, o may be 5, and all of R4 may be hydrogen.

[0110] In one embodiment of this specification, R4 may be deuterium.

[0111] In one embodiment of this specification, o may be 5, and all of R4 may be deuterium.

[0112] In one embodiment of this specification, o may be an integer from 1 to 6.

[0113] In one embodiment of this specification, Het is a group represented by any of the following chemical formulas H-1 to H-3. [ka]

[0114] In the above chemical formulas H-1 to H-3, Z is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. m is an integer between 0 and 4, and if m is 2 or greater, Z may be the same or different from each other. R5 and R6 are independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. p is an integer between 1 and 3, and q is an integer between 1 and 5. If both p and q are 2 or greater, R5 and R6 may be the same or different.

[0115] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0116] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0117] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0118] In one embodiment of this specification, Z may be hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C10 alkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted N-containing C2-C20 heteroaryl group.

[0119] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing a C=N bond.

[0120] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted pyridine group; or a substituted or unsubstituted pyrimidine group.

[0121] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a C1-C40 alkyl group substituted or unsubstituted with deuterium or a halogen group; a C6-C40 aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group or an alkyl group; or a C2-C40 heteroaryl group.

[0122] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a C1-C20 alkyl group substituted or unsubstituted with deuterium or a halogen group; a C6-C20 aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group or an alkyl group; or a C2-C20 heteroaryl group.

[0123] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a C1-C10 alkyl group substituted or unsubstituted with deuterium or a halogen group; a C6-C20 aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group or an alkyl group; or a C2-C20 heteroaryl group.

[0124] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a C1-C10 alkyl group substituted or unsubstituted with deuterium or a halogen group; a C6-C20 aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group or an alkyl group; or a C2-C20 heteroaryl group containing a C=N bond.

[0125] In one embodiment of this specification, Z may be hydrogen; deuterium; a halogen group; a cyano group; a halogen-substituted or unsubstituted methyl group; a deuterium-substituted or unsubstituted tert-butyl group; a deuterium-substituted or unsubstituted phenyl group; a naphthyl group; a pyridine group; or a pyrimidine group.

[0126] In one embodiment of this specification, Z may be hydrogen; deuterium; halogen group; cyano group; -CF3; deuterium-substituted or unsubstituted tert-butyl group; deuterium, halogen group, cyano group or tert-butyl group-substituted or unsubstituted phenyl group; naphthyl group; pyridine group; or pyrimidine group.

[0127] In one embodiment of this specification, m may be an integer from 1 to 4.

[0128] In one embodiment of this specification, m may be 1.

[0129] In one embodiment of this specification, if M, Ar, or Z is an alkyl group, then M, Ar, or Z may be a branched alkyl group of C2 to C10.

[0130] In one embodiment of this specification, R5 and R6 may each be independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; or a substituted or unsubstituted C2-C60 heterocycloalkyl group.

[0131] In one embodiment of this specification, R5 and R6 may each independently be hydrogen; deuterium; a halogen group; a cyano group; or a substituted or unsubstituted C1-C60 alkyl group.

[0132] In one embodiment of this specification, R5 and R6 may each be independently hydrogen; or deuterium.

[0133] In one embodiment of this specification, R5 may be hydrogen.

[0134] In one embodiment of this specification, p may be 3, and all of R5 may be hydrogen.

[0135] In one embodiment of this specification, R6 may be hydrogen.

[0136] In one embodiment of this specification, q may be 5, and all of R6 may be hydrogen.

[0137] In one embodiment of this specification, R5 may be deuterium.

[0138] In one embodiment of this specification, p is 3, and all of R5 may be deuterium.

[0139] In one embodiment of this specification, R6 may be deuterium.

[0140] In one embodiment of this specification, q is 5, and all of R6 may be deuterium.

[0141] In one embodiment of this specification, the sum of q and m in the chemical formula H-1 is an integer from 1 to 6.

[0142] In one embodiment of this specification, the sum of q and m in the chemical formula H-1 is 6.

[0143] In one embodiment of this specification, the sum of q and m in the chemical formula H-2 is an integer from 1 to 6.

[0144] In one embodiment of this specification, the sum of q and m in the chemical formula H-2 is 6.

[0145] In one embodiment of this specification, the sum of p and m in the chemical formula H-3 is an integer between 1 and 4.

[0146] In one embodiment of this specification, the sum of p and m in the chemical formula H-3 is 4.

[0147] In one embodiment of this specification, R4 to R6 may each be independently hydrogen or deuterium.

[0148] In one embodiment of this specification, the deuterium substitution rate based on total hydrogen and deuterium of the chemical formula 1 may be 0% or 5% to 100%.

[0149] In one embodiment of this specification, the deuterium substitution rate of chemical formula 1 may be 0% or 10% to 100%.

[0150] In one embodiment of this specification, the deuterium substitution rate of chemical formula 1 may be 0% or 15% to 100%.

[0151] In one embodiment of this specification, the deuterium substitution rate of chemical formula 1 may be 0% or 20% to 100%.

[0152] In one embodiment of this specification, the deuterium substitution rate of chemical formula 1 may be 0%.

[0153] In one embodiment of this specification, the deuterium substitution rate of chemical formula 1 may be 100%.

[0154] In this specification, the deuterium substitution rate means the ratio of the number of deuterium atoms to the total number of hydrogen atoms and deuterium atoms contained in a particular structure (e.g., chemical formula 1). For example, if a particular structure contains 20 hydrogen atoms and 20 deuterium atoms, the ratio of 20 deuterium atoms to the total of 40 hydrogen atoms and deuterium atoms is 50%, and therefore the deuterium substitution rate is 50%.

[0155] In one embodiment of this specification, as the deuterium ratio of the heterocyclic compound of chemical formula 1 satisfies the range, the photochemical characteristics of the heterocyclic compound of chemical formula 1 that does not contain deuterium and the compound that contains deuterium are substantially similar. However, when deposited on a thin film, the substance containing deuterium tends to be packed with a narrower intermolecular distance.

[0156] By fabricating EODs (Electron Only Devices) and HODs (Hole Only Devices) and confirming the current density with voltage, it can be confirmed that the heterocyclic compounds of the present invention that contain deuterium exhibit far more balanced charge transport characteristics than compounds without deuterium in the same structure.

[0157] Furthermore, when the surface of the thin film is examined with an atomic force microscope (AFM), it can be confirmed that the thin film made with a deuterium-containing compound was deposited on a more uniform surface without any aggregation (aggragate).

[0158] Furthermore, since the single bond dissociation energy between carbon and deuterium is higher than that between carbon and hydrogen, when the heterocyclic compound of chemical formula 1 of the present invention contains deuterium, the overall stability of the molecule increases, resulting in an improved device lifespan.

[0159] In one embodiment of this specification, the heterocyclic compound of chemical formula 1 can be represented by any of the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0160] Furthermore, by introducing various substituents into the structure of chemical formula 1, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0161] Furthermore, by introducing various substituents into the structure of chemical formula 1, it becomes possible to finely adjust the energy band gap, while simultaneously improving the properties at the interface between organic materials and diversifying the applications of the material.

[0162] In another embodiment of this specification, an organic light-emitting element is provided comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains one or more heterocyclic compounds of the chemical formula 1.

[0163] In one embodiment of this specification, the organic layer includes an electron transport layer, and the electron transport layer includes one or more heterocyclic compounds of chemical formula 1.

[0164] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light-emitting element is not limited thereto and may include fewer organic layers.

[0165] In one embodiment of this specification, the organic light-emitting element may include the first electrode, a first stack provided on the first electrode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and a second electrode provided on the second stack.

[0166] In this case, the charge generation layer may contain a heterocyclic compound represented by chemical formula 1. When the heterocyclic compound is used in the charge generation layer, the driving, efficiency, and lifespan of the organic light-emitting element can be improved. Specifically, the heterocyclic compound of the present invention can bind to metals, and its high binding effect with alkali metals or alkaline earth metals facilitates the injection of electrons generated from the P-type charge generation layer.

[0167] Furthermore, the first stack and the second stack may each independently further include one or more of the above-mentioned hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, etc.

[0168] In one embodiment of this specification, the organic light-emitting element includes a first electrode, a first stack provided on the first electrode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and a second electrode provided on the second stack, wherein the charge generation layer may contain one or more of the heterocyclic compounds.

[0169] In one embodiment of this specification, the charge generation layer is an N-type charge generation layer, and the N-type charge generation layer may contain one or more of the heterocyclic compounds.

[0170] In one embodiment of this specification, the charge generating layer may further contain a dopant known in the art in addition to the heterocyclic compound represented by chemical formula 1.

[0171] In one embodiment of this specification, the organic light-emitting element may further include a P-type charge generation layer.

[0172] As an example of an organic light-emitting element according to one embodiment of this application, an organic light-emitting element with a two-stack tandem structure is shown exemplified in Figure 4 below, but the application is not limited thereto, and additional organic layers may be provided.

[0173] In this case, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer shown in Figure 4 below may be omitted if necessary.

[0174] In one embodiment of this specification, the first electrode may be a positive electrode and the second electrode may be a negative electrode.

[0175] In another embodiment of this specification, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0176] An organic light-emitting element according to one embodiment of this specification can be manufactured by conventional methods and materials for manufacturing organic light-emitting elements, except that one or more organic layers are formed using the heterocyclic compound of chemical formula 1 described above.

[0177] The heterocyclic compound of chemical formula 1 may be formed in an organic layer not only by vacuum deposition during the manufacture of organic light-emitting devices, but also by solution coating methods. Here, solution coating methods include, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating.

[0178] In one embodiment of this specification, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound of chemical formula 1 can be used as a material for the blue organic light-emitting element. For example, the heterocyclic compound of chemical formula 1 may be included in the electron transport layer or charge generation layer of the blue organic light-emitting element.

[0179] In another embodiment of this specification, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound of chemical formula 1 can be used as a material for the green organic light-emitting element. For example, the heterocyclic compound of chemical formula 1 may be included in the electron transport layer or the charge generation layer of the green organic light-emitting element.

[0180] In another embodiment of this specification, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound of chemical formula 1 can be used as a material for the red organic light-emitting element. For example, the heterocyclic compound of chemical formula 1 may be included in the electron transport layer or the charge generation layer of the red organic light-emitting element.

[0181] The organic light-emitting element of the present invention may further include one or more layers selected from the group consisting of an emissive layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0182] Figures 1 to 4 illustrate the stacking sequence of electrodes and organic layers in an organic light-emitting element according to one embodiment of this specification. However, these figures are not intended to limit the scope of this application, and organic light-emitting element structures known in the art can also be applied to this application.

[0183] Figure 1 shows an organic light-emitting element in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to this, and an organic light-emitting element may be realized in which the negative electrode, organic material layer, and positive electrode are sequentially stacked on a substrate, as shown in Figure 2.

[0184] Figure 3 illustrates a case where the organic layers are multilayered. The organic light-emitting element according to Figure 3 includes a hole injection layer 301, a hole transport layer 302, an emissive layer 303, an electron transport layer 304, and an electron injection layer 305. However, the scope of this application is not limited by such a multilayer structure, and the remaining layers excluding the emissive layer may be omitted as needed, and other necessary functional layers may be added.

[0185] The organic layer containing the heterocyclic compound of chemical formula 1 may further contain other substances as needed.

[0186] In an organic light-emitting device according to one embodiment of this specification, materials other than the heterocyclic compound of chemical formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of this application, and can be replaced with materials known in the art.

[0187] As the positive electrode material, a material with a relatively large work function can be used, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the positive electrode material include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0188] As the negative electrode material, a material with a relatively low work function can be used, and may include metals, metal oxides, or conductive polymers. Specific examples of the negative electrode material include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0189] As the hole injection material, known hole injection materials can be used, but for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4”-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), or a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0190] As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., can be used, and low molecular weight or high molecular weight materials may be used.

[0191] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives can be used, and not only low molecular weight substances but also high molecular weight substances may be used.

[0192] LiF (LiFuminescence) is a typical electron injection material used in this industry, but this application is not limited to it.

[0193] Red, green, and blue light-emitting materials can be used, and two or more light-emitting materials may be mixed and used as needed. In this case, the two or more light-emitting materials may be deposited as separate sources, or they may be pre-mixed and deposited as a single source. Fluorescent materials can also be used as light-emitting materials, as can phosphorescent materials. As light-emitting materials, materials that emit light by combining holes and electrons injected from the positive and negative electrodes, respectively, can be used individually, or materials in which both the host material and the dopant material participate in light emission can be used.

[0194] When using a mixture of hosts for the light-emitting material, hosts from the same series may be mixed, or hosts from different series may be mixed. For example, two or more types of N-type host materials or P-type host materials may be selected and used as the host material for the light-emitting layer.

[0195] An organic light-emitting element according to one embodiment of this specification may be a front-emitting type, a rear-emitting type, or a double-sided emitting type, depending on the material used.

[0196] The compounds according to one embodiment of this specification can also operate in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, using the same principles as those applied to organic light-emitting devices.

[0197] Furthermore, by introducing various substituents into the structure of chemical formula 1, the energy band gap can be finely adjusted, while simultaneously improving the properties at the interface between organic materials, thereby diversifying the applications of the material.

[0198] Another embodiment of this specification provides a method for manufacturing an organic light-emitting element, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using an organic layer composition, and the organic layer composition comprises the heterocyclic compound of chemical formula 1 described above. [Examples]

[0199] The Specification will be described in more detail below through examples, which are for illustrative purposes only and not intended to limit the scope of this application.

[0200] <Manufacturing example> <Manufacturing Example 1> Manufacturing of Compound 1 [ka]

[0201] 1) Preparation of compound 1-1 Compound A (2-bromo-9-phenyl-1,10-phenanthroline) (50g, 0.149mol, 1eq), (3-cholrophenyl)boronic acid (26.2g, 0.164mol, 1.1eq), Pd(PPh3)4 (8.61g, 0.007mol, 0.05eq), K2CO3 (41.2g, 0.298mol, 2.0eq), Toluene (500ml), EtOH (ethanol) (100ml), and Water (100ml) were added and stirred at 100°C for 6 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was obtained to obtain 49.2g of compound 1-1 with a yield of 90%.

[0202] 2) Preparation of Compound 1-2 Compound 1-1 (49.1 g, 0.134 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (37.8 g, 0.147 mol, 1.1 eq), Pd2(dba)3 (4.23 g, 0.007 mol, 0.05 eq), Xphos (6.38 g, 0.013 mmol, 0.1 eq), KOAc (potassium acetate) (32.8 g, 0.335 mol, 2.5 eq), and 1,4-Dioxane (375 ml) were added and stirred at 100°C for 6 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Compounds 1 and 2 were separated using a silica gel column to obtain 48.0 g of each compound with a yield of 78%.

[0203] 3) Preparation of compounds 1-3 Compound 1-2 (26.0 g, 0.057 mol, 1 eq), 1-(6-bromo-2-pyridyl)ethanone (12.5 g, 0.062 mol, 1.1 eq), Pd(PPh3)4 (3.29 g, 0.003 mol, 0.05 eq), K2CO3 (15.8 g, 0.114 mol, 2.0 eq), 1,4-dioxane (250 ml), and water (50 ml) were added and stirred at 100°C for 10 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was performed to obtain 20.2 g of compound 1-3 with a yield of 79%.

[0204] 4) Preparation of Compound 1 Compounds 1-3 (20.0 g, 0.045 mol, 1 eq), compound B (2-aminobenzaldehyde) (10.7 g, 0.089 mol, 2.0 eq), NaOH (5.32 g, 0.133 mol, 3.0 eq), and IPA (isopropyl alcohol) (200 ml) were added and stirred at 90°C for 24 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was performed to obtain 10.5 g of compound 1 with a yield of 44%.

[0205] In the above-mentioned Production Example 1, the compounds shown in Table 1 below were synthesized in the same manner using intermediates A and B shown in Table 1 below, respectively, instead of compounds A and B.

[0206] [Table 1]

[0207] <Manufacturing Example 2> Manufacturing of Intermediate C [ka]

[0208] 2-amino-5-bromobenzaldehyde (30.0 g, 0.150 mol, 1 eq), phenylboronic acid (21.9 g, 0.180 mol, 1.2 eq), Pd(PPh3)4 (8.67 g, 0.008 mol, 0.05 eq), K2CO3 (41.5 g, 0.300 mol, 2.0 eq), 1,4-dioxane (300 ml), and water (60 ml) were added and stirred at 100°C for 5 hours. After terminating the reaction with distilled water, the mixture was extracted with dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Intermediate C, 26.1 g, was obtained by separation using a silica gel column with an 88% yield.

[0209] Depending on the structure to be synthesized, 2-amino-4-bromobenzaldehyde or 2-amino-6-bromobenzaldehyde was used instead of 2-amino-5-bromobenzaldehyde in Production Example 2, and pyridin-2-ylboronic acid or pyridin-4-ylboronic acid was used instead of phenylboronic acid, and they were synthesized in the same manner to obtain Intermediate C in Table 2 below.

[0210] <Production Example 3> Production of Compound 8

Chemical formula

[0211] Compound 1-3 (20.0 g, 0.045 mol, 1 eq) produced in Production Example 1, Compound C (17.8 g, 0.089 mmol) produced in Production Example 2, NaOH (5.32 g, 0.133 mol, 3.0 eq), and IPA (200 ml) were added, and the mixture was stirred at 90 °C for 24 hours. After adding distilled water to terminate the reaction, extraction was performed using dichloromethane and distilled water. Then, water was removed with MgSO4. Separation was carried out using a silica gel column to obtain 14.7 g of Compound 8 in a yield of 53%.

[0212] The compound obtained by synthesizing in the same manner as in Production Example 1 using Intermediate A in Table 2 below instead of Compound A in Production Example 1 was used instead of Compound 1-3 in Production Example 3, and Intermediate C in Table 2 below was used instead of Compound C in Production Example 3, and the compounds in Table 2 below were obtained by synthesizing in the same manner.

[0213]

Table 2

[0214]

Table 3

[0215] <Manufacturing Example 4> Manufacturing of Intermediate C 1) Intermediate C of compounds 145, 146, 150, 156, 161, 162, 168, 171, 173, 191, 209, 212, and 214 [ka]

[0216] 1-(6-bromo-2-pyridyl)ethanone (20.0 g, 0.100 mol, 1 eq), 2-aminobenzaldehyde (12.1 g, 0.100 mol, 1.0 eq), NaOH (6.00 g, 0.150 mol, 1.5 eq), and EtOH (200 ml) were added and stirred at 160°C for 2 hours. After terminating the reaction with distilled water, the mixture was extracted with dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Intermediate C, 17.3 g, was obtained by separation using a silica gel column with a yield of 61%.

[0217] Depending on the structure to be synthesized, intermediate C shown in Table 3 below was obtained by synthesizing in the same manner as in Production Example 4, using 3-amino-[1,1'-biphenyl]-4-carbaldehyde, 2-amino-5-(pyridin-2-yl)benzaldehyde, or 2-amino-4-(pyridin-2-yl)benzaldehyde instead of 2-aminobenzaldehyde.

[0218] 2) Intermediate C of compound 321 [ka]

[0219] (2-chloroquinolin-7-yl)boronic acid (30.0 g, 0.145 mol, 1 eq), 2-bromopyridine (25.1 g, 0.159 mol, 1.1 eq), Pd(PPh3)4 (8.38 g, 0.007 mol, 0.05 eq), K2CO3 (40.1 g, 0.290 mol, 2.0 eq), 1,4-Dioxane (300 ml), and Water (60 ml) were added and stirred at 100°C for 4 hours. After terminating the reaction with distilled water, the mixture was extracted with dichloromethane and distilled water. Then, water was removed with MgSO4. The mixture was separated by silica gel column chromatography to obtain 25.3 g of intermediate C with a yield of 72%.

[0220] <Manufacturing Example 5> Manufacturing of Compound 145 [ka]

[0221] 1) Preparation of compound 145-1 Compound A (2-bromo-9-phenyl-1,10-phenanthroline) (30 g, 0.089 mol, 1 eq), 2-(3-bromo-5-chloro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.2 g, 0.098 mol, 1.1 eq), Pd(PPh3)4 (5.14 g, 0.004 mol, 0.05 eq), K3PO4 (38.0 g, 0.179 mol, 2.0 eq), 1,4-Dioxane (300 ml), and Water (60 ml) were added and stirred at 100°C for 3 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Compound 145-1 was separated using a silica gel column to obtain 32.9 g with an 83% yield.

[0222] 2) Preparation of compound 145-2 Compound 145-1 (25.0 g, 0.056 mol, 1 eq), Compound B (phenyl boronic acid) (7.68 g, 0.062 mol, 1.1 eq), Pd(PPh₃)₄ (3.24 g, 0.003 mol, 0.05 eq), Na₂CO₃ (11.9 g, 0.112 mol, 2.0 eq), 1,4-dioxane (250 ml), and Water (50 ml) were added, and the mixture was stirred at 100 °C for 10 hours. After adding distilled water to terminate the reaction, extraction was performed using dichloromethane and distilled water. Then, the water was removed with MgSO₄. Separation was carried out using a silica gel column to obtain 22.0 g of Compound 145-2 in an 89% yield.

[0223] 3) Preparation of Compound 145-3 Compound 145-2 (22.0 g, 0.050 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.0 g, 0.055 mol, 1.1 eq), Pd₂(dba)₃ (1.43 g, 0.002 mol, 0.05 eq), XPhos (2.37 g, 0.005 mmol, 0.1 eq), KOAc (12.2 g, 0.124 mol, 2.5 eq), and 1,4-dioxane (250 ml) were added, and the mixture was stirred at 100 °C for 6 hours. After adding distilled water to terminate the reaction, extraction was performed using dichloromethane and distilled water. Then, the water was removed with MgSO₄. Separation was carried out using a silica gel column to obtain 19.0 g of Compound 145-3 in a 72% yield.

[0224] 4) Preparation of Compound 145 Compound 145-3 (18.0 g, 0.034 mol, 1 eq), compound C (2-(6-bromopyridin-2-yl)quinoline) (9.82 g, 0.041 mol, 1.2 eq), Pd(PPh3)4 (1.95 g, 0.002 mol, 0.05 eq), K2CO3 (9.31 g, 0.067 mol, 2.0 eq), 1,4-dioxane (200 ml), and water (40 ml) were added and stirred at 100°C for 24 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was obtained to obtain 13.0 g of compound 145 with a yield of 63%.

[0225] The compounds shown in Table 3 below were synthesized in the same manner as in Production Example 5, except that intermediates A to C in Table 3 below were used instead of compounds A to C.

[0226] [Table 4]

[0227] [Table 5]

[0228] [Table 6]

[0229] <Manufacturing Example 6> Manufacturing of Compound 147 [ka]

[0230] Compound 147 was synthesized in the same manner as in Production Example 5, except that in the production of compound 145-1 of Production Example 5, 2-(3-bromo-5-(tert-butyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(3-bromo-5-chloro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0231] In the above-mentioned production example 6, the compounds shown in Table 4 below were obtained by synthesizing them in the same manner using intermediates A and B shown in Table 4 below instead of compounds A and B.

[0232] [Table 7]

[0233] <Manufacturing Example 7> Manufacturing of Intermediate B [ka]

[0234] 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (30.0 g, 0.125 mol, 1 eq), 3-chloroisoquinoline (22.5 g, 0.138 mol, 1.1 eq), Pd(PPh3)4 (7.22 g, 0.006 mol, 0.05 eq), K2CO3 (34.6 g, 0.250 mol, 2.0 eq), 1,4-Dioxane (300 ml), and Water (60 ml) were added, and the mixture was stirred at 100°C for 4 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Intermediate B, 23.3 g, was obtained by separation using a silica gel column with a yield of 77%.

[0235] Depending on the structure to be synthesized, intermediate B shown in Table 5 was obtained by synthesizing in the same manner as in Production Example 7, using 3-chloroisoquinoline instead of 3-chloroisoquinoline, with either 3-chloro-7-phenylisoquinoline or 1-chloroisoquinoline.

[0236] <Manufacturing Example 8> Manufacturing of Compound 232 [ka]

[0237] 1) Preparation of compound 232-1 Compound A (2-bromo-9-phenyl-1,10-phenanthroline) (50 g, 0.149 mol, 1 eq), (3-cholrophenyl)boronic acid (26.2 g, 0.164 mol, 1.1 eq), Pd(PPh3)4 (8.61 g, 0.007 mol, 0.05 eq), K2CO3 (41.2 g, 0.298 mol, 2.0 eq), Toluene (500 ml), EtOH (100 ml), and Water (100 ml) were added and the mixture was stirred at 100°C for 6 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was obtained to obtain 49.2 g of compound 232-1 with a yield of 90%.

[0238] 2) Preparation of compound 232-2 Compound 232-1 (49.1 g, 0.134 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (37.8 g, 0.147 mol, 1.1 eq), Pd2(dba)3 (4.23 g, 0.007 mol, 0.05 eq), Xphos (6.38 g, 0.013 mmol, 0.1 eq), KOAc (32.8 g, 0.335 mol, 2.5 eq), and 1,4-Dioxane (375 ml) were added, and the mixture was stirred at 100°C for 6 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Compound 232-2 was separated using a silica gel column to obtain 48.0 g with a yield of 78%.

[0239] 3) Preparation of compound 232 Compound 232-2 (15.0 g, 0.033 mol, 1 eq), Compound B (3-(6-chloropyridin-2-yl)isoquinoline) (8.66 g, 0.036 mol, 1.1 eq), Pd(PPh3)4 (1.92 g, 0.002 mol, 0.05 eq), K2CO3 (9.12 g, 0.066 mol, 2.0 eq), 1,4-Dioxane (150 ml), and Water (30 ml) were added and stirred at 100°C for 24 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was performed to obtain 15.0 g of Compound 232 with an 85% yield.

[0240] In the above-mentioned production example 8, the compounds were synthesized in the same manner using intermediate A from Table 5 below instead of compounds A and B, and intermediate B instead of 3-(6-chloropyridin-2-yl)isoquinoline (B), to obtain the compounds shown in Table 5 below.

[0241] [Table 8]

[0242] <Manufacturing Example 9> Manufacturing of Compound 306 [ka]

[0243] 1) Preparation of compound 306-1 (3-acetylphenyl)boronic acid (20 g, 0.122 mol, 1 eq), compound A (2-amino-4-bromobenzaldehyde) (24.4 g, 0.122 mol, 1.0 eq), NaOH (7.32 g, 0.183 mol, 1.5 eq), and EtOH (ethanol) (200 ml) were added and the mixture was stirred at 60°C for 2 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Compound 306-1, 34.0 g, was obtained by separation using a silica gel column with an 85% yield.

[0244] 2) Preparation of compound 306-2 Compound 306-1 (28.3g, 0.086mol, 1.2eq), Compound B (2-bromo-9-phenyl-1,10-phenanthroline) (25.0g, 0.75mol, 1.0eq), Pd2(dba)3 (4.30g, 0.004mol, 0.05eq), K2CO3 (20.6g, 0.149mol, 2.0eq), 1,4-Dioxane (300ml), and Water (60ml) were added and stirred at 100°C for 6 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Compound 306-2, 34.0g, was obtained by separation using a silica gel column with a yield of 84%.

[0245] 3) Preparation of compound 306 Compound 306-2 (15.0 g, 0.028 mol, 1 eq), compound C (pyridin-2-ylboronic acid) (3.77 g, 0.031 mol, 1.1 eq), Pd(PPh3)4 (1.61 g, 0.001 mol, 0.05 eq), K2CO3 (7.70 g, 0.056 mol, 2.0 eq), 1,4-Dioxane (150 ml), and water (30 ml) were added and stirred at 100°C for 16 hours. After terminating the reaction with distilled water, the mixture was extracted using dichloromethane and distilled water. Subsequently, water was removed with MgSO4. Separation by silica gel column was obtained to obtain 7.0 g of compound 306 with a yield of 47%.

[0246] In the above-mentioned production example 9, the compounds shown in Table 6 below were obtained by synthesizing them in the same manner using intermediates A to C shown in Table 6 below instead of compounds A to C.

[0247] [Table 9]

[0248] <Manufacturing Example 10> Manufacturing of Compound 401

[0249] [ka]

[0250] Compound 1 (5g, 0.01mol, 1eq) from Preparation Example 1, Triflic acid (5.76ml, 0.065mol, 7eq), and C6D6 (25ml) were added and stirred at 60°C for 2 hours. After adding D2O and stirring for 30 minutes, triethylamine was added dropwise to neutralize the mixture. After neutralization, the mixture was extracted using dichloromethane. Subsequently, water was removed with MgSO4. Compound 401, 3.4g, was obtained by separation using a silica gel column with a yield of 65%.

[0251] <Manufacturing Example 11> Manufacturing of Compound 402 [ka]

[0252] In the above-mentioned production example 10, compound 405 was synthesized using the same method with compound 145 from production example 5 instead of compound 1.

[0253] <Manufacturing Example 12> Manufacturing of Compound 411 [ka]

[0254] In the above-mentioned production example 10, compound 411 was synthesized using the same method with compound 306 from production example 9 instead of compound 1.

[0255] The compound synthesized by the above manufacturing example is 1 The synthesis of the desired compound was confirmed via 1H-NMR and FD-mass spectrometry. 1 The 1H NMR (CDCl3, 200MHz) measurements are listed in Table 7 below, and the FD-mass spectrometer (FD-Mass: Field desorption mass spectrometry) measurements are listed in Table 8 below.

[0256] [Table 10]

[0257] [Table 11]

[0258] [Table 12]

[0259] [Table 13]

[0260] [Table 14]

[0261] [Table 15]

[0262] [Table 16]

[0263] <Example of experiment> <Experimental Example 1> 1) Fabrication of organic light-emitting devices <Comparative Example 1> A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, then stored in isopropanol before use. Next, the ITO substrate was placed in the substrate holder of the vacuum deposition apparatus, and the following 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell inside the vacuum deposition apparatus. [ka]

[0264] Next, the vacuum level inside the chamber is 10 -6 After evacuating until the torr level was reached, an electric current was applied to the cell to evaporate 2-TNATA and deposit a 600 Å thick hole injection layer onto the ITO substrate. In another cell within the vacuum deposition apparatus, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed, and an electric current was applied to the cell to evaporate it, depositing a 300 Å thick hole transport layer on top of the hole injection layer. [ka]

[0265] After forming the hole injection layer and hole transport layer in this manner, a blue light-emitting material with the following structure was deposited on top of them as a light-emitting layer. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å in one cell of the vacuum deposition apparatus, and a blue light-emitting dopant material, D1, was vacuum-deposited on top of it at a thickness of 5% relative to the host material. [ka]

[0266] Next, a compound with the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer. [ka]

[0267] An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as the electron injection layer and using an Al anode to a thickness of 1,000 Å. Meanwhile, all the organic compounds necessary for fabricating the OLED device were prepared by material, each taking 10 -8 ~10 -6 The material was purified by vacuum sublimation under Torr conditions and used for OLED fabrication.

[0268] <Examples 1-50, Comparative Examples 2-11> An organic light-emitting element was fabricated in the same manner as in Comparative Example 1, except that the compound shown in Table 9 below was used instead of E1, which was used when forming the electron transport layer in Comparative Example 1.

[0269] The structures of the comparative compounds used in Comparative Examples 2 to 11 are as follows. [ka]

[0270] 2) Driving voltage and luminous efficiency of organic light-emitting element For the organic light-emitting device manufactured as described above, the electroluminescence (EL) characteristics were measured using Mac Science's M7000, and based on the measurement results, the reference luminance was 3,500 cd / m 2 when it is, T 95 was measured. The measured results of the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan (T 95 ) of the blue organic electroluminescent device manufactured according to the present invention were as shown in Table 9.

[0271]

Table 17

[0272]

Table 18

[0273] As can be seen from the results in Table 9 above, the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device of the present invention had a lower driving voltage, and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 11.

[0274] The reason for such results is judged that the skeleton of the present invention has an appropriate electron transport ability, and due to the stable bond between the phenanthroline functional group and the metal used for the negative electrode, a more stable compound is such that the decomposition or destruction of the compound does not occur and electrons can be efficiently transmitted.

[0275] In particular, the comparative compounds A to J used in Comparative Examples 2 to 11 contain a partial structure of the heterocyclic compound of the present invention but do not satisfy Chemical Formula 1 of the present invention. Specifically, comparative compounds A to D and H to J are different from the Het configuration of the present invention, comparative compound E is different from the Het position of the present invention, comparative compound F does not contain the M configuration of the present invention, and comparative compound G contains a naphthalene ring instead of the benzene ring of the present invention.

[0276] This confirmed that even if some of the structures in the heterocyclic compound structure of the present invention are adopted similarly, if the overall configuration of the present invention is not satisfied, it will not be able to provide superior effects as a device compared to the heterocyclic compound of the present invention.

[0277] When comparing specific numerical values, comparative examples 2 to 11, which use compounds containing similar structures but are not within the scope of the present invention, showed some improvement in terms of luminous efficiency and lifetime compared to comparative example 1 using compound E1. However, the maximum luminous efficiency was 7.12 cd / A and the maximum lifetime remained at 72.

[0278] On the other hand, in Examples 1 to 53, which used the compound of the present invention, the luminous efficiency was 7.54 to 7.84 cd / A and the lifetime was 95 to 129 days. Compared to the conventional material (Comparative Example 1), the luminous efficiency increased by at least 17% and the lifetime increased by at least 1.9 times. Furthermore, compared to the comparative example group, it can be seen that there were further improvements of at least 5% in terms of luminous efficiency and at least 30% in terms of lifetime.

[0279] Therefore, the heterocyclic compound of the present invention, by satisfying all the components of Chemical Formula 1, is judged to have improved electron transport properties and stability compared to similar structures, and to be superior in all aspects of drive voltage, efficiency, and lifespan.

[0280] <Experimental Example 2> 1) Fabrication of organic light-emitting devices A glass substrate coated with a thin ITO film to a thickness of 1500 Å was cleaned using distilled water ultrasonic cleaning. After distilled water cleaning, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, followed by drying. Then, UVO treatment was performed using UV light in a UV cleaning machine for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaning machine (PT), where it under vacuum plasma treatment was performed to determine the ITO work function and remove any remaining film, before being transferred to a thermal deposition apparatus for organic vapor deposition.

[0281] Organic material was formed on the aforementioned ITO transparent electrode (positive electrode) in a two-stack WOLED (White Organic Light Device) structure. For the first stack, a hole transport layer was first formed by thermal vacuum deposition of TAPC to a thickness of 300 Å. After forming the hole transport layer, a light-emitting layer was deposited on top of it as follows: The light-emitting layer was deposited at 300 Å by doping TCz1, the host, with 8% Firpic as a blue phosphorescent dopant. For the electron transport layer, a 400 Å layer was formed using TmPyPB, and then a 100 Å layer was formed as a charge generation layer by doping the compounds listed in Table 10 below with 20% Cs2CO3.

[0282] For the second stack, a hole injection layer was first formed by thermal vacuum deposition of MoO3 to a thickness of 50 Å. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO3 to a thickness of 100 Å, followed by deposition of TAPC to a thickness of 300 Å. On top of that, the light-emitting layer was formed by doping the host TCz1 with 8% green phosphorescent dopant Ir(ppy)3 to a thickness of 300 Å, followed by the formation of an electron transport layer using TmPyPB to a thickness of 600 Å. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) anode was deposited to a thickness of 1,200 Å on the electron injection layer to form the anode, thereby fabricating an organic electroluminescent device. [ka]

[0283] The comparative compounds in Table 10 below have the same structure as those in Experimental Example 1.

[0284] On the other hand, all the organic compounds required for fabricating OLED elements are 10 each, depending on the material. -8 ~10 -6 The material was purified by vacuum sublimation under Torr conditions and used for OLED fabrication.

[0285] 2) Driving voltage and luminous efficiency of organic light-emitting element For the organic electroluminescent element manufactured as described above, the electroluminescent (EL) characteristics were measured using MacScience's M7000, and the measurement results were used to determine if the reference brightness was 3,500 cd / m² through a lifetime measurement device (M6000) manufactured by MacScience. 2 At that time, T 95 The following were measured: the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime (T) of a white organic electroluminescent element manufactured according to the present invention. 95 The results of the measurements are shown in Table 10.

[0286] [Table 19]

[0287] [Table 20]

[0288] As can be seen from the results in Table 10 above, the organic electroluminescent element using the charge generation layer material of the two-stack white organic electroluminescent element of the present invention had a lower driving voltage, improved lifespan and luminous efficiency compared to Comparative Examples 12 to 22.

[0289] The reason for these results is believed to be that the framework has a structure with appropriate electron transport capability and is composed of phenanthroline functional groups that can bind to metals such as Li and Yb used in the formation of the N-type charge generation layer.

[0290] Due to these structural characteristics, when the compound used as the N-type charge generation layer is doped with metal, a stable gap state is formed within the N-type charge generation layer. This facilitates electron injection from the P-type charge generation layer into the electron transport layer via the gap state formed within the N-type charge generation layer. Therefore, electron injection from the P-type charge generation layer to the N-type charge generation layer, followed by electron transfer to the electron transport layer, is efficiently performed, resulting in a lower driving voltage for the organic light-emitting element and improved efficiency and lifetime.

[0291] Furthermore, as described above in Experimental Example 1, the comparative compounds used in Comparative Examples 12 to 22 contain configurations that differ only in some structural aspects from the heterocyclic compound of the present invention. However, it was confirmed that when used as charge generation layer materials, they do not exhibit superior effects compared to the present invention.

[0292] This confirmed that even if some of the structures in the heterocyclic compound structure of the present invention are adopted similarly, if the overall configuration of the present invention is not satisfied, it will not be able to provide superior effects as a device compared to the heterocyclic compound of the present invention. [Explanation of Symbols]

[0293] 100 ··· circuit board 200...Positive electrode 300...organic layer 301 ···Hole injection layer 302 ···Hole transport layer 303 ···Luminous layer 304...electron transport layer 305...electron injection layer 400...Negative electrode

Claims

1. Heterocyclic compounds of the following chemical formula 1: 【Chemistry 1】 In the aforementioned chemical formula 1, M is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group. Ar is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. R1 to R3 are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; or substituted or unsubstituted C2-C60 heterocycloalkyl group. R4 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group. o is an integer from 0 to 6, and if o is 2 or greater, R4 may be the same or different. Het is a group represented by one of the following chemical formulas H-1 to H-3: 【Chemistry 2】 In the above chemical formulas H-1 to H-3, Z is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. m is an integer from 0 to 4, and if m is 2 or greater, Z may be the same or different from each other. R5 and R6 are independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. p is an integer from 1 to 3, and q is an integer from 1 to 5. If both p and q are 2 or greater, R5 and R6 may be the same or different.

2. The aforementioned chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3, the heterocyclic compound according to claim 1: 【Transformation 3】 【Chemistry 4】 In the above chemical formulas 1-1 to 1-3, The definitions of each substituent are the same as those in Chemical Formula 1 above.

3. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulas: 1-1-1, 1-1-2, 1-2-1, or 1-3-1: 【Transformation 5】 【Transformation 6】 In the aforementioned chemical formulas 1-1-1, 1-1-2, 1-2-1, and 1-3-1, The definitions of each substituent are the same as those in Chemical Formula 1 above.

4. The heterocyclic compound according to claim 1, wherein Ar is hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing O or S.

5. The heterocyclic compound according to claim 1, wherein M is a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

6. The heterocyclic compound according to claim 1, wherein Z is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C10 alkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heteroaryl group.

7. The heterocyclic compound according to claim 1, wherein each of the R1 to R3 is independently hydrogen; or deuterium.

8. The heterocyclic compound according to claim 1, wherein each of the R4 to R6 is independently hydrogen; or deuterium.

9. The heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 0% or 10% to 100%.

10. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any of the following compounds: 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 。

11. first electrode; Second electrode; and One or more organic layers provided between the first electrode and the second electrode An organic light-emitting element comprising, An organic light-emitting element wherein at least one of the organic layers contains one or more heterocyclic compounds as described in any one of claims 1 to 10.

12. The aforementioned organic layer includes an electron transport layer, The organic light-emitting element according to claim 11, wherein the electron transport layer comprises one or more of the heterocyclic compounds.

13. The aforementioned organic light-emitting device is First electrode, A first stack, including a first light-emitting layer, is provided on the first electrode. A charge generation layer provided on the first stack, A second stack, including a second light-emitting layer, is provided on the charge generation layer, and The second electrode provided on the second stack Includes, The organic light-emitting element according to claim 11, wherein the charge generation layer comprises one or more of the heterocyclic compounds.

14. The organic light-emitting element according to claim 13, wherein the charge generation layer is an N-type charge generation layer, and the N-type charge generation layer contains at least one of the heterocyclic compounds.

Images