Organic light-emitting element and composition for forming organic material layer

Abstract

The present specification provides an organic light-emitting element and a composition for an organic material layer of the organic light-emitting element.

Description

Technical Field

[0001] This specification relates to an organic light-emitting device and a composition for forming an organic material layer.

[0002] This application claims the priority and benefit of Korean Patent Application No. 10-2022-0159372, filed with the Korean Intellectual Property Office on November 24, 2022, the entire contents of which are incorporated herein by reference. Background Art

[0003] An electroluminescence (EL) device is a self-emitting display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined into pairs in the organic thin film, and then the paired electrons and holes emit light while annihilating. The organic thin film may be composed of a single layer or multiple layers as needed.

[0005] The material for the organic thin film may have a light-emitting function as needed. For example, as the material for the organic thin film, a compound that can form a light-emitting layer alone by itself may be used, or a compound that can be used as a host or a dopant for a host-dopant-based light-emitting layer may also be used. In addition, as the material for the organic thin film, a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may also be used.

[0006] In order to improve the performance, efficiency, and service life of organic light-emitting devices, there has been a continuous need to develop materials for organic thin films. Summary of the Invention

[0007] Technical Problem

[0008] This specification is directed to providing an organic light-emitting device and a composition for forming an organic material layer.

[0009] Technical Solution

[0010] This specification provides an organic light-emitting device, including: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 below.

[0011] [Chemical Formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] X is O or S,

[0015] L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene,

[0016] Z1 is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, N - Het is a substituted or unsubstituted monocyclic or polycyclic C2 - C60 heteroaryl containing one or more Ns,

[0017] R1 to R6 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0018] a and b are each an integer from 0 to 3, and when a is 2 or greater than 2, L1s are the same as or different from each other, and when b is 2 or greater than 2, L2s are the same as or different from each other,

[0019] p and t1 are each an integer from 1 to 3, and when p is 2 or greater than 2, Z1s are the same as or different from each other, and when t1 is 2 or greater than 2, N - Hets are the same as or different from each other,

[0020] [Chemical Formula 2]

[0021]

[0022] In Chemical Formula 2,

[0023] L3 and L4 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted C6 - C60 arylene,

[0024] Z2 and Z3 are each independently a substituted or unsubstituted amino group; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0025] Either of Z2 and Z3 is a substituted or unsubstituted amino group, and the other is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0026] R7 and R8 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; -CN; 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,

[0027] c and d are each an integer from 0 to 3, and when c is 2 or greater than 2, L3s are the same as or different from each other, and when d is 2 or greater than 2, L4s are the same as or different from each other,

[0028] p2 and p3 are each an integer from 1 to 3, and when p2 is 2 or greater than 2, Z2s are the same as or different from each other, and when p3 is 2 or greater than 2, Z3s are the same as or different from each other,

[0029] r is an integer from 0 to 5, and when r is 2 or greater than 2, R7s are the same as or different from each other, and

[0030] s is an integer from 0 to 3, and when s is 2 or greater than 2, R8s are the same as or different from each other.

[0031] In addition, this specification provides a composition for forming an organic material layer, and the composition includes a compound of Formula 1 and a compound of Formula 2.

[0032] Advantageous Effects

[0033] The organic light-emitting device of this specification includes an organic material layer including a compound of Formula 1 and a compound of Formula 2, and the organic material layer including the compound can be a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, and similar layers. In particular, the organic material layer including the compound can be the light-emitting layer of the organic light-emitting device.

[0034] When the compound of Formula 1 and the compound of Formula 2 are used together as materials for the light-emitting layer of the organic light-emitting device, the driving voltage of the device can be reduced, the luminous efficiency can be improved, and the service life characteristics can be improved.

[0035] Specifically, when the compound of Formula 1, which is an acceptor (n-type host) having good electron transport ability, and the compound of Formula 2, which is a donor (p-type host) having good hole transport ability, are used as co-hosts of the light-emitting layer, since electrons and holes are smoothly injected into the light-emitting layer, the driving voltage can be reduced, and the efficiency and service life of the device can be improved by forming an effective recombination zone (RZ). Description of the Drawings

[0036] Figures 1 to 4 are diagrams each schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.

[0037]

Description of Symbols

[0038] 100: Substrate

[0039] 200: Positive electrode

[0040] 300: Organic material layer

[0041] 301: Hole injection layer

[0042] 302: Hole transport layer

[0043] 303: Light-emitting layer

[0044] 304: Hole blocking layer

[0045] 305: Electron transport layer

[0046] 306: Electron injection layer

[0047] 307: Electron blocking layer

[0048] 400: Negative electrode Detailed implementation manners

[0049] In the following, this specification will be elaborated in more detail.

[0050] In this specification, when a component "includes" a constituent element, unless otherwise specifically elaborated, this does not mean excluding another constituent element, but rather means that another constituent element may also be included.

[0051] In this specification, in the chemical formula means the position to which the constituent element is bonded.

[0052] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the position to be substituted is not restricted as long as the position is the position where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0053] In this specification, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, -CN, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 haloalkyl, C1-C60 alkoxy, C6-C60 aryloxy, C1-C60 alkylthioxy, C6-C60 arylthioxy, C1-C60 alkylsulfonyloxy, C6-C60 arylsulfonyloxy, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, -SiRR'R", -P(=O)RR', and -NRR', or a substituent linked to a substituent selected from two or more of the exemplified substituents, and R, R', and R" are each independently a substituent composed of at least one of hydrogen, deuterium, a halogen group, alkyl, alkenyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl.

[0054] In this specification, "when no substituent is specified in the chemical formula or the structure of the compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium (2H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0055] In an exemplary embodiment of the present application, "when no substituent is specified in the chemical formula or the structure of the compound" may mean that all positions accessible to the substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium as an isotope, and in such a case, the content of deuterium may be 0% to 100%.

[0056] In an exemplary embodiment of the present application, in the case of "when no substituent is specified in the chemical formula or the structure of the compound", when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents do not explicitly exclude deuterium (e.g., hydrogen), hydrogen and deuterium may be mixed and used in the compound.

[0057] In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuteron composed of one proton and one neutron as its nucleus, and can be represented by hydrogen-2, and the element symbol can also be expressed as D or 2H.

[0058] In an exemplary embodiment of the present application, an isotope means an atom having the same atomic number (Z) but having a different mass number (A), and an isotope can also be interpreted as an element having the same number of protons but having a different number of neutrons.

[0059] In an exemplary embodiment of the present application, when the total number of substituents of the base compound is defined as T1, and the number of a specific substituent among the substituents is defined as T2, the content T% of the specific substituent can be defined as T2 / T1×100 = T%.

[0060] That is, in an example, when the total number of substituents that a phenyl group can have is 5 (T1 in the formula) and the number of deuteriums among the substituents is 1 (T2 in the formula), the deuterium content of 20% in the phenyl group represented by can be represented by 20%. That is, the deuterium content of 20% in the phenyl group can be represented by the following structural formula.

[0061]

[0062] In addition, in an exemplary embodiment of the present application, "a phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain deuterium atoms (i.e., has five hydrogen atoms).

[0063] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0064] In this specification, the alkyl group includes a straight-chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and similar groups, but are not limited thereto.

[0065] In this specification, the alkenyl group includes a straight-chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of the alkenyl group include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styryl, and similar groups, but are not limited thereto.

[0066] In this specification, alkynyl includes straight-chain or branched-chain groups having 2 to 60 carbon atoms, and may be further substituted with another substituent. The number of carbon atoms in alkynyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0067] In this specification, haloalkyl means an alkyl group substituted with a halogen group, and specific examples of haloalkyl include -CF3, -CF2CF3, and similar groups, but are not limited thereto.

[0068] In this specification, alkoxy is represented by -O(R101), and the above examples of alkyl groups are applicable to R101.

[0069] In this specification, aryloxy is represented by -O(R102), and the above examples of aryl groups are applicable to R102.

[0070] In this specification, alkylthioxy is represented by -S(R103), and the above examples of alkyl groups are applicable to R103.

[0071] In this specification, arylthioxy is represented by -S(R104), and the above examples of aryl groups are applicable to R104.

[0072] In this specification, alkylsulfonyloxy is represented by -S(=O)2(R105), and the above examples of alkyl groups are applicable to R105.

[0073] In this specification, arylsulfonyloxy is represented by -S(=O)2(R106), and the above examples of aryl groups are applicable to R106.

[0074] In this specification, cycloalkyl includes monocyclic or polycyclic groups having 3 to 60 carbon atoms, and may be further substituted with another substituent. Here, polycyclic means a group in which cycloalkyl is directly linked or fused with another cyclic group. Here, another cyclic group may also be cycloalkyl, but may also be another type of cyclic group, such as heterocycloalkyl, aryl, heteroaryl, and similar groups. The number of carbon atoms in cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and similar groups, but are not limited thereto.

[0075] In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with another substituent. Herein, the polycyclic group means a group in which the heterocycloalkyl group is directly linked or fused to another cyclic group. Herein, the other cyclic group may also be a heterocycloalkyl group, but may also be another kind of cyclic group, such as a cycloalkyl group, an aryl group, a heteroaryl group and similar groups. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0076] In the present specification, the aryl group includes a monocyclic or polycyclic group having 6 to 60 carbon atoms, and may be further substituted with another substituent. Herein, the polycyclic group means a group in which the aryl group is directly linked or fused to another cyclic group. Herein, the other cyclic group may also be an aryl group, but may also be another kind of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group and similar groups. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a terrylene group, a picenyl group, a pyrenyl group, a condensed tetraphenyl group, a condensed pentaphenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzo[h]fluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, its fused ring group and similar groups, but not limited thereto.

[0077] In the present specification, the terphenyl group may be selected from the following structures.

[0078]

[0079] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0080] When the fluorenyl group is substituted, the substituent may be and similar groups, but not limited thereto.

[0081] In the present specification, a heteroaryl contains S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Herein, a polycyclic group means a group in which a heteroaryl is directly linked or fused to another cyclic group. Herein, another cyclic group may also be a heteroaryl, but may also be another type of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and similar groups. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thiophene group, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxin group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazoline group, isoquinazolinyl, quinozoline group, naphthyridinyl, acridinyl, phenanthridine group, imidazopyridyl, phthalazinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilole group, spirobis(dibenzosilole), dihydro phenazinyl, phenoxazinyl, phenanthridine group, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindolyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazine group, phthalazinyl, phenanthrolinyl, naphthobenzofuryl, naphthobenzothienyl, benzo[c][1,2,5]thiadiazolyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzofuryl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, 12H-benzofuro[2,3-a]carbazolyl, benzofuro[3,2-d]pyrimidinyl, benzo[4,5]thieno[3,2-d]pyrimidinyl, and similar groups, but are not limited thereto.

[0082] In the present specification, when the substituent is a carbazolyl group, it means bonding to the nitrogen or carbon of the carbazole.

[0083] In this specification, when the carbazolyl group is substituted, the additional substituent may be substituted by the nitrogen or carbon of the carbazole.

[0084] In this specification, the benzocarbazolyl group may be any of the following structures.

[0085]

[0086] In this specification, the dibenzocarbazolyl group may be any of the following structures.

[0087]

[0088] In this specification, the naphthobenzofuranyl group may be any of the following structures.

[0089]

[0090] In this specification, the naphthobenzothienyl group may be any of the following structures.

[0091]

[0092] In this specification, the silyl group contains Si and is a substituent directly bonded to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same or different from each other, and may each independently be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specific examples of the silyl group include (trimethylsilyl), (triethylsilyl), (tert-butyldimethylsilyl), (vinyldimethylsilyl), (propyldimethylsilyl), (triphenylsilyl), (diphenylsilyl), (phenylsilyl) and similar groups, but are not limited thereto.

[0093] In this specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same or different from each other, and may each independently be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specifically, the phosphine oxide group may be substituted by an alkyl group or an aryl group, and the above examples may be applicable to the alkyl group and the aryl group. Examples of the phosphine oxide group include dimethylphosphine oxide group, diphenylphosphine oxide group, dinaphthylphosphine oxide, and similar groups, but are not limited thereto.

[0094] In this specification, an amino group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amino group is optionally selected from the group consisting of -NH2, a monoalkylamino group, a monoarylamino group, a monoheteroarylamino group, a dialkylamino group, a diarylamino group, a diheteroarylamino group, an alkylarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, and the number of carbon atoms of the amino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, a dibiphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a xylanylamino group, a phenyltolylamino group, a triphenylamino group, a biphenylnaphthylamino group, a phenylbiphenylamino group, a biphenylfluorenylamino group, a phenylterphenylamino group, a biphenylterphenylamino group, and similar groups, but are not limited thereto.

[0095] In this specification, the above examples of the aryl group are applicable to an arylene group other than a divalent arylene group.

[0096] In this specification, the above examples of the heteroaryl group are applicable to a heteroarylene group other than a divalent heteroarylene group.

[0097] In this specification, an "adjacent" group may mean a substituent substituted by an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent substituted by the atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0098] The hydrocarbon rings and heterocyclic rings that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and the structures exemplified by the above cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group are applicable to rings other than rings that are not monovalent groups.

[0099] In an exemplary embodiment of the present application, a group not represented by a substituent or a group represented by hydrogen may mean that all can be substituted by deuterium. That is, it can indicate that hydrogen and deuterium can substitute each other.

[0100] Generally, a compound hydrogen-bonded and a deuterium-substituted compound exhibit differences in thermodynamic behavior. The reason is that the mass of a deuterium atom is 2 times higher than the mass of hydrogen, but due to the difference in atomic mass, deuterium is characterized by having an even lower vibration energy.

[0101] In addition, the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, the structure substituted with deuterium has the effect of improving the thermal stability of the molecule and using the improved thermal stability to improve the service life of the device.

[0102] When the compound is deposited on a silicon wafer, the material containing deuterium tends to pack, resulting in a reduced intermolecular distance. In addition, when observing the surface of the thin film using an atomic force microscope (AFM), it can be confirmed that the thin film made of the compound containing deuterium has a more uniform surface deposition without any aggregated portion.

[0103] The heterocyclic compound of Chemical Formula 1 in the present application has a deuterium substitution rate of 0% or 30% to 100% or less than 100%. The deuterium-substituted compound is characterized in that the ground state energy is lower than that of the hydrogen-substituted compound, and the shorter the bond length between carbon and deuterium, the smaller the molecular hardcore volume. Therefore, the electrical polarizability can be reduced and the intermolecular interaction can be weakened, such that when manufacturing a device, the device has a more stable stacked structure.

[0104] These characteristics cause the effect of reducing crystallinity by generating an amorphous state of the thin film. That is, the heterocyclic compound represented by Chemical Formula 1 can effectively improve the heat resistance of an organic light emitting diode (OLED) device, thereby improving the service life and driving characteristics.

[0105] The present application provides an organic light emitting device including: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer contains a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2.

[0106] [Chemical Formula 1]

[0107]

[0108] In Chemical Formula 1,

[0109] X is O or S,

[0110] L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene,

[0111] Z1 is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, N - Het is a substituted or unsubstituted monocyclic or polycyclic C2 - C60 heteroaryl containing one or more Ns,

[0112] R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0113] a and b are each an integer from 0 to 3, and when a is 2 or greater than 2, L1s are the same as or different from each other, and when b is 2 or greater than 2, L2s are the same as or different from each other,

[0114] p and t1 are each an integer from 1 to 3, and when p is 2 or greater than 2, Z1s are the same as or different from each other, and when t1 is 2 or greater than 2, N - Hets are the same as or different from each other,

[0115] [Chemical formula 2]

[0116]

[0117] In Chemical formula 2,

[0118] L3 and L4 are the same as or different from each other, and each independently is a direct bond; or a substituted or unsubstituted C6 - C60 arylene,

[0119] Z2 and Z3 are different from each other, and each independently is a substituted or unsubstituted amino group; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0120] Either Z2 or Z3 is a substituted or unsubstituted amino group, and the other is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0121] R7 and R8 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0122] c and d are each an integer from 0 to 3, and when c is 2 or greater than 2, L3s are the same as or different from each other, and when d is 2 or greater than 2, L4s are the same as or different from each other,

[0123] p2 and p3 are each an integer from 1 to 3, and when p2 is 2 or higher, Z2s are the same as or different from each other, and when p3 is 2 or higher, Z3s are the same as or different from each other.

[0124] r is an integer from 0 to 5, and when r is 2 or higher, R7s are the same as or different from each other, and

[0125] s is an integer from 0 to 3, and when s is 2 or higher, R8s are the same as or different from each other.

[0126] When the compound of Chemical Formula 1 and the compound of Chemical Formula 2 included in this specification together are used as materials for the organic material layer of an element, electrons and holes move in a well-balanced manner such that the recombination region (RZ) is widely located at the center of the light-emitting layer, thereby achieving excellent driving, efficiency, and service life of the element.

[0127] In an exemplary embodiment of this application, Chemical Formula 1 can be represented by any one of the following Chemical Formula 1-1 and Chemical Formula 1-2.

[0128] [Chemical Formula 1-1]

[0129]

[0130] [Chemical Formula 1-2]

[0131]

[0132] In Chemical Formula 1-1 and Chemical Formula 1-2,

[0133] X, R1 to R6, L1, L2, Z1, N-Het, a, b, p, and t1 are the same as defined in Chemical Formula 1.

[0134] In an exemplary embodiment of this application, N-Het can be represented by the following Chemical Formula 3.

[0135] [Chemical Formula 3]

[0136]

[0137] In Chemical Formula 3,

[0138] X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, and X5 is CR15 or N,

[0139] at least one of X1 to X5 is N, and

[0140] R11 to R15 are the same as or different from each other, and each independently selected from the group consisting of: hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and an amino group unsubstituted or substituted by a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0141] In an exemplary embodiment of the present application, Chemical Formula 3 can be represented by any one of the following Chemical Formulas 3-1 to 3-3.

[0142] [Chemical Formula 3-1]

[0143]

[0144] [Chemical Formula 3-2]

[0145]

[0146] [Chemical Formula 3-3]

[0147]

[0148] In Chemical Formulas 3-1 to 3-3,

[0149] X6 to X9 are each N or CR16,

[0150] At least one of X6 to X8 is N,

[0151] A and B are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl ring; or a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic ring, and

[0152] R16 and R61 to R64 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0153] In an exemplary embodiment of the present application, Chemical Formula 3-1 can be selected from the following structural formulas.

[0154]

[0155] The definitions of R61 and R62 are the same as those in Chemical Formula 3-1.

[0156] In an exemplary embodiment of the present application, Chemical Formula 3-2 can be represented by any one of the following Chemical Formulas 3-2-1 to 3-2-3.

[0157] [Chemical Formula 3-2-1]

[0158]

[0159] [Chemical Formula 3-2-2]

[0160]

[0161] [Chemical Formula 3-2-3]

[0162]

[0163] In Chemical Formulas 3-2-1 to 3-2-3, R63 is the same as defined in Chemical Formula 3-2, and R71 to R82 are the same as or different from each other, and each independently is hydrogen; or deuterium.

[0164] In an exemplary embodiment of the present application, Chemical Formula 3-3 can be represented by the following Chemical Formula 3-3-1.

[0165] [Chemical Formula 3-3-1]

[0166]

[0167] In Chemical Formula 3-3-1, R64 is the same as defined in Chemical Formula 3-3, and

[0168] R83 to R86 are the same as or different from each other, and each independently is hydrogen; or deuterium.

[0169] In an exemplary embodiment of the present application, L1 and L2 are the same as or different from each other, and each can independently be a direct bond; a substituted or unsubstituted C6-C40 arylene; or a substituted or unsubstituted C2-C40 heteroarylene.

[0170] In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each can independently be a direct bond; a substituted or unsubstituted C6-C20 arylene; or a substituted or unsubstituted C2-C20 heteroarylene.

[0171] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other, and each can independently be a direct bond; or a substituted or unsubstituted C6-C20 arylene.

[0172] In yet a further exemplary embodiment, L1 and L2 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0173] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other, and may each independently be a direct bond; a phenylene; or a naphthylene.

[0174] In an exemplary embodiment of the present application, Z1 may be a substituted or unsubstituted C6-C40 aryl; or a substituted or unsubstituted C2-C40 heteroaryl.

[0175] In another exemplary embodiment, Z1 may be a substituted or unsubstituted C6-C20 aryl; or a substituted or unsubstituted C2-C20 heteroaryl.

[0176] In yet another exemplary embodiment, Z1 may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted terrylene; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted naphthobenzothiophenyl; or a substituted or unsubstituted carbazolyl.

[0177] In yet another exemplary embodiment, Z1 may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted naphthobenzofuranyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[0178] In yet another exemplary embodiment, Z1 may be an unsubstituted or deuterium-substituted phenyl; an unsubstituted or deuterium-substituted biphenyl; an unsubstituted or deuterium-substituted naphthyl; a deuterium-substituted or unsubstituted phenanthryl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted naphthobenzofuranyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[0179] In an exemplary embodiment of the present application, R1 to R6 are the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1-C20 alkyl; a substituted or unsubstituted C6-C20 aryl; or a substituted or unsubstituted C2-C20 heteroaryl.

[0180] In another exemplary embodiment, R1 to R6 are the same as or different from each other, and each may independently be hydrogen; or deuterium.

[0181] In an exemplary embodiment of the present application, a and b are each an integer from 0 to 2, and when a is 2, L1 are the same as or different from each other, and when b is 2, L2 may be the same as or different from each other.

[0182] In another exemplary embodiment, a and b may each be 0 or 1.

[0183] In an exemplary embodiment of the present application, p and t1 are each an integer from 1 to 2, and when p is 2, Z1 are the same as or different from each other, and when t1 is 2, N-Het may be the same as or different from each other.

[0184] In another exemplary embodiment, p and t1 may each be 1.

[0185] In an exemplary embodiment of the present application, N-Het may be a monocyclic or polycyclic C2-C40 heteroaryl group that is substituted or unsubstituted and contains one or more Ns.

[0186] In another exemplary embodiment, N-Het may be a monocyclic or polycyclic C2-C20 heteroaryl group that is substituted or unsubstituted and contains one or more Ns.

[0187] In yet another exemplary embodiment, N-Het may be a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyrimidinyl group; a substituted or unsubstituted triazinyl group; a substituted or unsubstituted quinazolinyl group; a substituted or unsubstituted quinoxalinyl group; a substituted or unsubstituted benzofuranopyrimidinyl group; or a substituted or unsubstituted benzothiophenopyrimidinyl group.

[0188] In yet another exemplary embodiment, N-Het may be: a pyrimidinyl group substituted with deuterium, an unsubstituted or naphthyl-substituted phenyl group, a biphenyl group, an unsubstituted or phenyl-substituted naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a naphthobenzofuranyl group; a triazinyl group substituted with an unsubstituted or deuterium-substituted or unsubstituted or deuterium-substituted phenyl group, a naphthyl group, a phenanthryl group, an unsubstituted or dibenzofuranyl- or carbazolyl-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, deuterium, an unsubstituted or deuterium-substituted or unsubstituted or deuterium-substituted phenyl group, a naphthyl group, an unsubstituted or phenyl-substituted phenanthryl group, a group, a dibenzofuranyl group which is unsubstituted or substituted with deuterium or phenyl, a dibenzothiophenyl group, a naphthobenzofuranyl group which is unsubstituted or substituted with deuterium, a naphthobenzothiophenyl group, or a carbazolyl group which is unsubstituted or substituted with phenyl; a quinazolinyl group substituted with phenyl, naphthyl, dibenzofuranyl, naphthobenzofuranyl or naphthobenzothiophenyl; a quinoxalinyl group substituted with biphenyl or phenanthryl; a benzofuranopyrimidinyl group substituted with phenyl, naphthyl, biphenyl, dibenzofuranyl or naphthobenzofuranyl; or a benzothiophenopyrimidinyl group substituted with phenyl, biphenyl or naphthyl.

[0189] In an exemplary embodiment of the present application, X6 to X8 may all be N.

[0190] In an exemplary embodiment of the present application, X9 may be N.

[0191] In an exemplary embodiment of the present application, A may be a substituted or unsubstituted benzene ring; a substituted or unsubstituted quinoline ring; a substituted or unsubstituted indole ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring.

[0192] In another exemplary embodiment, A may be a benzene ring; a quinoline ring; an indole ring substituted with an aryl group; a benzofuran ring; or a benzothiophene ring.

[0193] In an exemplary embodiment of the present application, B may be a substituted or unsubstituted monocyclic aryl ring.

[0194] In another exemplary embodiment, B may be a benzene ring.

[0195] In an exemplary embodiment of the present application, R16 and R61 to R64 are the same as or different from each other, and may each independently 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.

[0196] In another exemplary embodiment, R16 and R61 to R64 are the same as or different from each other, and may each independently 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.

[0197] In yet another exemplary embodiment, R16 and R61 to R64 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted a group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted naphthobenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0198] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 1% to 100%.

[0199] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 10% to 100%.

[0200] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 15% to 100%.

[0201] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 30% to 100%.

[0202] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 50% to 100%.

[0203] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 70% to 100%.

[0204] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0% or 90% to 100%.

[0205] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0%.

[0206] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 15% to 100%.

[0207] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 30% to 100%.

[0208] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 50% to 100%.

[0209] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 70% to 100%.

[0210] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 90% to 100%.

[0211] In an exemplary embodiment of the present application, a heterocyclic compound is provided, in which Formula 1 is represented by any one of the following compounds.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] In an exemplary embodiment of the present application, Z2 and Z3 are each independently a substituted or unsubstituted amino group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, and either of Z2 and Z3 is a substituted or unsubstituted amino group, and the other may be a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0237] In another exemplary embodiment, Z2 and Z3 are each independently a substituted or unsubstituted amino group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, and either of Z2 and Z3 is a substituted or unsubstituted amino group, and the other may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0238] In yet another exemplary embodiment, Z2 and Z3 are each independently an amino group substituted with a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and either of Z2 and Z3 is an amino group substituted with a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group, and the other may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0239] In yet another exemplary embodiment, Z2 and Z3 are each independently an amino group substituted with a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group; an unsubstituted or deuterium-substituted phenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothiophenyl group, and either of Z2 and Z3 is an amino group substituted with a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, and the other may be an unsubstituted or deuterium-substituted phenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0240] In an exemplary embodiment of the present application, L3 and L4 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6-C40 arylene group.

[0241] In yet another exemplary embodiment, L3 and L4 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

[0242] In yet another exemplary embodiment, L3 and L4 are the same as or different from each other, and can each independently be a direct bond; a substituted or unsubstituted phenylene; or a substituted or unsubstituted naphthylene.

[0243] In yet another exemplary embodiment, L3 and L4 are the same as or different from each other, and can each independently be a direct bond; an unsubstituted or deuterium-substituted phenylene; or a naphthylene.

[0244] In an exemplary embodiment of the present application, R7 and R8 are the same as or different from each other, and can each independently be hydrogen; deuterium; a halogen group; -CN; 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.

[0245] In another exemplary embodiment, R7 and R8 are the same as or different from each other, and can each independently be hydrogen; deuterium; a halogen group; -CN; 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.

[0246] In yet another exemplary embodiment, R7 and R8 are the same as or different from each other, and can each independently be hydrogen; or deuterium.

[0247] In an exemplary embodiment of the present application, c and d are each an integer from 0 to 2, and when c is 2, L3 are the same as or different from each other, and when d is 2, L4 can be the same as or different from each other.

[0248] In another exemplary embodiment, c and d can each be 0 or 1.

[0249] In an exemplary embodiment of the present application, c and d are each an integer from 0 to 2, and when c is 2, L3 are the same as or different from each other, and when d is 2, L4 can be the same as or different from each other.

[0250] In another exemplary embodiment, c and d can be 1.

[0251] In an exemplary embodiment of the present application, r and s are each an integer from 0 to 2, and when s is 2, R7 are the same as or different from each other, and when t is 2, R8 can be the same as or different from each other.

[0252] In another exemplary embodiment, r and s can each be 0 or 1.

[0253] In an exemplary embodiment of the present application, p2 and p3 are each an integer from 1 to 2, and when p2 is 2, Z2 are the same as or different from each other, and when p3 is 2, Z3 can be the same as or different from each other.

[0254] In another exemplary embodiment, p2 and p3 can be 1.

[0255] In an exemplary embodiment of the present application, r is an integer from 0 to 4, and when r is 2 or higher, R7 can be the same as or different from each other.

[0256] In another exemplary embodiment, r is an integer from 0 to 3, and when r is 2 or higher, R7 can be the same as or different from each other.

[0257] In yet another exemplary embodiment, r is an integer from 0 to 2, and when r is 2, R7 can be the same as or different from each other.

[0258] In yet another exemplary embodiment, r can be 1.

[0259] In an exemplary embodiment of the present application, s is an integer from 0 to 3, and when s is 2 or higher, R8 can be the same as or different from each other.

[0260] In another exemplary embodiment, s is an integer from 0 to 2, and when s is 2, R8 can be the same as or different from each other.

[0261] In yet another exemplary embodiment, s can be 1.

[0262] In an exemplary embodiment of the present application, Chemical Formula 2 can be represented by the following Chemical Formula 2-1 or Chemical Formula 2-2.

[0263] [Chemical Formula 2-1]

[0264]

[0265] [Chemical Formula 2-2]

[0266]

[0267] In Chemical Formula 2-1 and Chemical Formula 2-2,

[0268] L3, L4, R7, R8, c, d, r and s are the same as defined in Chemical Formula 2,

[0269] Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0270] Z4 and Z5 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0271] p4 and p5 are each an integer from 1 to 3, and when p4 is 2 or higher, Z4s are the same as or different from each other, and when p5 is 2 or higher, Z5s are the same as or different from each other.

[0272] In an exemplary embodiment of the present application, Z4 and Z5 can each independently be a substituted or unsubstituted C6 - C40 aryl group; or a substituted or unsubstituted C2 - C40 heteroaryl group.

[0273] In another exemplary embodiment, Z4 and Z5 can each independently be a substituted or unsubstituted C6 - C20 aryl group; or a substituted or unsubstituted C2 - C20 heteroaryl group.

[0274] In yet another exemplary embodiment, Z4 and Z5 can each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0275] In yet another exemplary embodiment, Z4 and Z5 can each independently be an unsubstituted or deuterium - substituted phenyl group; naphthyl group; dibenzofuranyl group; or dibenzothiophenyl group.

[0276] In an exemplary embodiment of the present application, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C40 aryl group; or a substituted or unsubstituted C2 - C40 heteroaryl group.

[0277] In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C20 aryl group; or a substituted or unsubstituted C2 - C20 heteroaryl group.

[0278] In yet another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and can each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzofuranyl group; or a substituted or unsubstituted naphthobenzothiophenyl group.

[0279] In yet another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each may independently be an unsubstituted or deuterium-, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenanthryl, dibenzofuranyl or dibenzothiophenyl-substituted phenyl; an unsubstituted or deuterium- or dibenzofuranyl-substituted biphenyl; an unsubstituted or deuterium-substituted terphenyl; an unsubstituted or deuterium- or unsubstituted or deuterium-substituted phenyl-substituted naphthyl; an unsubstituted or substituted with one or more selected from the group consisting of deuterium, alkyl and aryl fluorenyl; an unsubstituted or deuterium-substituted dibenzofuranyl; dibenzothiophenyl; naphthobenzofuranyl; or naphthobenzothiophenyl.

[0280] In an exemplary embodiment of the present application, either of Ar1 and Ar2 is a substituted or unsubstituted C6-C40 aryl, and the other may be a substituted or unsubstituted C6-C40 aryl; or a substituted or unsubstituted C2-C40 heteroaryl.

[0281] In an exemplary embodiment of the present application, either of Ar3 and Ar4 is a substituted or unsubstituted C6-C40 aryl, and the other may be a substituted or unsubstituted C6-C40 aryl; or a substituted or unsubstituted C2-C40 heteroaryl.

[0282] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 1% to 100%.

[0283] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 10% to 100%.

[0284] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 15% to 100%.

[0285] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 30% to 100%.

[0286] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 50% to 100%.

[0287] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 70% to 100%.

[0288] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0% or 90% to 100%.

[0289] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be 0%.

[0290] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be from 15% to 100%.

[0291] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be from 30% to 100%.

[0292] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be from 50% to 100%.

[0293] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be from 70% to 100%.

[0294] In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 2 may be from 90% to 100%.

[0295] In an exemplary embodiment of the present application, a compound is provided, in which Formula 2 is represented by any one of the following compounds.

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309] In an exemplary embodiment of the present application, the compound is only one example and is not limited thereto, and may include other compounds with additional substituents included in Chemical Formula 1 and Chemical Formula 2. Additionally, the substitution positions of deuterium in the compound may exist while specific positions are excluded, and hydrogen and deuterium are mixed during the process of deuterium substitution and synthesis.

[0310] Furthermore, compounds having the inherent properties of substituents introduced by introducing various substituents into the structures of Chemical Formula 1 and Chemical Formula 2 can be synthesized. For example, substituents commonly used for hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used when manufacturing organic light-emitting devices can be introduced into the core structure to synthesize materials that meet the requirements of each organic material layer.

[0311] In addition, by introducing various substituents into the structures of Chemical Formula 1 and Chemical Formula 2 or changing the bonding positions, the band gap can be finely adjusted, and at the same time, the properties at the interface between organic material layers can be improved.

[0312] Furthermore, the compounds of Chemical Formula 1 and Chemical Formula 2 have excellent thermal stability, and such thermal stability provides driving stability for organic light-emitting devices and improves the service life characteristics.

[0313] In an exemplary embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer may include the compound of Chemical Formula 1 and the compound of Chemical Formula 2. That is, the compounds of Chemical Formula 1 and Chemical Formula 2 can be used as light-emitting materials for the light-emitting layer of an organic light-emitting device.

[0314] In another exemplary embodiment, the compounds of Chemical Formula 1 and Chemical Formula 2 can be used as host materials for the light-emitting layer of an organic light-emitting device.

[0315] In an exemplary embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0316] In another exemplary embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0317] In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the compounds according to Chemical Formula 1 and Chemical Formula 2 can be used as materials for the blue organic light-emitting device.

[0318] In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the compounds according to Chemical Formula 1 and Chemical Formula 2 can be used as materials for the green organic light-emitting device.

[0319] In an exemplary embodiment of the present application, the organic light-emitting element may be a red organic light-emitting element, and the compounds according to Chemical Formula 1 and Chemical Formula 2 may be used as materials for the red organic light-emitting element.

[0320] In an exemplary embodiment of the present application, the organic light-emitting element may be a blue organic light-emitting element, and the compounds according to Chemical Formula 1 and Chemical Formula 2 may be used as materials for the light-emitting layer of the blue organic light-emitting element.

[0321] In an exemplary embodiment of the present application, the organic light-emitting element may be a green organic light-emitting element, and the compounds according to Chemical Formula 1 and Chemical Formula 2 may be used as materials for the light-emitting layer of the green organic light-emitting element.

[0322] In an exemplary embodiment of the present application, the organic light-emitting element may be a red organic light-emitting element, and the compounds according to Chemical Formula 1 and Chemical Formula 2 may be used as materials for the light-emitting layer of the red organic light-emitting element.

[0323] In addition to the above heterocyclic compounds being used to form the organic material layer having one or more layers, the organic light-emitting element of the present invention can be manufactured using typical manufacturing methods and materials of the organic light-emitting element.

[0324] When manufacturing the organic light-emitting element, the heterocyclic compound can be formed into the organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and similar methods, but is not limited thereto.

[0325] The organic material layer of the organic light-emitting element of the present invention may be constituted by a single-layer structure, but may also be constituted by a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and similar layers as the organic material layer. However, the structure of the organic light-emitting element is not limited thereto, but may include a smaller number of organic material layers.

[0326] In an exemplary embodiment of the present application, as an iridium-based dopant, Ir(ppy)3 which is a green phosphorescent dopant can be used.

[0327] In an exemplary embodiment of the present application, as an iridium-based dopant, (piq)2(Ir)(acac) which is a red phosphorescent dopant can be used.

[0328] In the organic light-emitting device of the present application, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may contain a compound of Formula 1, a compound of Formula 2, or a combination thereof.

[0329] In another organic light-emitting device, the organic material layer includes a hole blocking layer, and the hole blocking layer may contain a compound of Formula 1, a compound of Formula 2, or a combination thereof.

[0330] In yet another organic light-emitting device, the organic material layer includes an electron blocking layer, and the electron blocking layer may contain a compound of Formula 1, a compound of Formula 2, or a combination thereof.

[0331] In yet another organic light-emitting device, the organic material layer includes a hole transport layer, a light-emitting layer, or an electron blocking layer, and the hole transport layer, the light-emitting layer, or the electron blocking layer may contain a compound of Formula 1, a compound of Formula 2, or a combination thereof.

[0332] In still another organic light-emitting device, the organic material layer includes a hole transport layer or a hole transport assisting layer, and the hole transport layer or the hole transport assisting layer may contain a compound of Formula 1, a compound of Formula 2, or a combination thereof.

[0333] In the organic light-emitting device of the present application, as the positive electrode material, a material having a relatively high work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, and similar materials can be used. Specific examples of the positive electrode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and similar materials, but not limited thereto.

[0334] As the negative electrode material, a material having a relatively low work function can be used, and a metal, a metal oxide, a conductive polymer, and similar materials can be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al; and similar materials, but not limited thereto.

[0335] As the hole injection material, known hole injection materials can also be used. For example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 can be used; or starburst amine derivatives described in the document [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), polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (which are soluble conductive polymers), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate), and similar materials.

[0336] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives and similar materials can be used, and low molecular weight materials or polymer materials can also be used.

[0337] As the electron transport material, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and similar materials can be used, and low molecular weight materials and polymer materials can also be used.

[0338] As the electron injection material, for example, LiF is typically used in this technology, but the present application is not limited thereto.

[0339] As the light-emitting material, red, green or blue light-emitting materials can be used, and if necessary, two or more light-emitting materials can be mixed and used. In this case, two or more light-emitting materials are deposited as or used as separate supply sources, or are premixed to be deposited as and used as one supply source. In addition, fluorescent materials can also be used as the light-emitting material, but can also be used as phosphorescent materials. As the light-emitting material, materials that emit light by combining holes and electrons injected from the positive electrode and the negative electrode respectively can also be used alone, but materials in which the host material and the dopant material participate in light emission together can also be used.

[0340] When the host of the luminescent material is mixed and used, hosts of the same series may also be mixed and used, and hosts of different series may also be mixed and used. For example, two or more types of materials selected from n-type host materials or p-type host materials may be used as the host material of the light-emitting layer.

[0341] Depending on the materials to be used, the organic light-emitting device according to an exemplary embodiment of the present application may be a top emission type, a bottom emission type, or a dual emission type.

[0342] The compound of Formula 1 and the compound of Formula 2 according to an exemplary embodiment of the present application may function even in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and similar devices, based on a principle similar to the principle applied to the organic light-emitting device.

[0343] The organic light-emitting device of the present invention may further include one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0344] In another exemplary embodiment, the compound represented by Formula 1 may be used as the luminescent material of the light-emitting layer of the organic light-emitting device and may be used as an n-type host material.

[0345] In yet another exemplary embodiment, the heterocyclic compound represented by Formula 2 may be used as the luminescent material of the light-emitting layer of the organic light-emitting device and may be used as a p-type host material.

[0346] In the organic light-emitting device of the present application, the organic material layer may contain the compound represented by Formula 1 and the compound represented by Formula 2. The organic material layer may be formed by premixing the compound represented by Formula 1 and the compound represented by Formula 2 and using a thermal vacuum deposition method.

[0347] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, the method including: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming an organic material layer having one or more layers using a composition of the organic material layer according to an exemplary embodiment of the present application.

[0348] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, in which the organic material layer is formed by supplying a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 as each separate supply source and then forming the organic material layer using a thermal vacuum deposition method.

[0349] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, in which the organic material layer is formed by premixing a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0350] Figures 1 to 4 The stacking order of the electrodes and the organic material layer of the organic light-emitting device according to the exemplary embodiment of the present application is exemplified. However, the scope of the present application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art may also be applicable to the present application.

[0351] According to Figure 1 , an organic light-emitting device is shown in which a positive electrode (200), an organic material layer (300), and a negative electrode (400) are stacked on a substrate (100) in sequence. However, the organic light-emitting device is not limited to such a structure, and as in Figure 2 , an organic light-emitting device in which a negative electrode, an organic material layer, and a positive electrode are stacked on a substrate in sequence can also be implemented.

[0352] Figure 3 And 4 The case where the organic material layer is multilayered is exemplified.

[0353] According to Figure 3 , the organic light-emitting device includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306).

[0354] According to Figure 4 , the organic light-emitting device includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (307), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306).

[0355] However, the scope of the present application is not limited by the stacking structure as described above, and other layers except the light-emitting layer can be omitted as needed, and another necessary functional layer can be further added.

[0356] In an exemplary embodiment of the present application, a composition for forming an organic material layer is provided, and the composition includes a compound of Chemical Formula 1 and a compound of Chemical Formula 2.

[0357] The compound of Chemical Formula 1 and the compound of Chemical Formula 2 in the composition for forming an organic material layer are the same as those defined in Compound 1 and Compound 2 above.

[0358] The composition for forming an organic material layer according to an exemplary embodiment of the present application may include the compound of Chemical Formula 1 and the compound of Chemical Formula 2 in a weight ratio of 1:10 to 10:1, particularly in a weight ratio of 1:5 to 5:1 and 1:3 to 3:1.

[0359] The composition for forming an organic material layer according to an exemplary embodiment of the present application can be used as a material for the light-emitting layer of an organic light-emitting device.

[0360] When forming the organic material layer of an organic light-emitting device, the composition can be used, and specifically, the composition can be better used as a host material for the light-emitting layer.

[0361] The composition is in the form of a simple mixture of two or more compounds, and the materials in powder form can also be mixed before forming the organic material layer of the organic light-emitting device, and the compounds in liquid form can be mixed at a temperature equal to or higher than the suitable temperature. The composition is in a solid state at a temperature equal to or lower than the melting point of each material, and can be maintained in a liquid phase when the temperature is adjusted.

[0362] The composition may further include materials known in the art, such as solvents and additives.

[0363] Hereinafter, the present specification will be described in more detail by examples, but the examples are provided only for exemplifying the present application and are not intended to limit the scope of the present application.

[0364] <Synthesis Example>

[0365] Preparation Example 1. Preparation of Compounds 1-4

[0366]

[0367] Preparation Example 1-1. Preparation of Compounds 1-2-4

[0368] After 30.0 g (106.6 mmol / L (mM)) of 3-bromo-1-chlorodibenz[b,d]furan, 26.4 g (106.6 mmol / L) of (4-(naphthalen-2-yl)phenyl)boronic acid, 6.2 g (5.3 mmol / L) of Pd(PPh3)4, and 29.5 g (213.2 mmol / L) of K2CO3 were placed into a 1 L two-necked flask and dissolved in 1,4-dioxane / H2O (300 mL / 600 mL), the resulting solution was refluxed for 1 hour. The reaction product was purified by column chromatography (dichloromethane (DCM): hexane (Hex) = 1:1), and 36.5 g (84.6%) of the target compound 1-2-4 was obtained.

[0369] Preparation Example 1-2. Preparation of Compound 1-1-4

[0370] After 36.0 g (88.9 mmol / L) of compound 1-2-4, 33.9 g (133.4 mmol / L) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (4.4 mmol / L) of Pd(dba)2, 3.7 g (8.9 mmol / L) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos), and 17.4 g (177.8 mmol / L) of KOAc were placed into a 1 L two-necked flask and dissolved in 1,4-dioxane (350 mL), the resulting solution was refluxed for 1 hour. The reaction product was purified by column chromatography (DCM: hexane = 1:4), and 35.3 g (80.0%) of the target compound 1-1-4 was obtained.

[0371] Preparation Example 1-3. Preparation of Compound 1-4

[0372] After 8.0 g (16.1 mmol / L) of compound 1-1-4, 4.3 g (16.1 mmol / L) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.9 g (0.8 mmol / L) of Pd(PPh3)4, and 4.5 g (32.2 mmol / L) of K2CO3 were placed into a 250 mL two-necked flask and dissolved in 1,4-dioxane / H2O (80 mL / 15 mL), the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 8.3 g (85.7%) of the target compound 1-4 was obtained.

[0373] Except for using Intermediate A in Table 1 below instead of (4-(naphthalen-2-yl)phenyl)boronic acid in Preparation Example 1 and using Intermediate B in Table 1 below instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, the target compounds in Table 1 below were synthesized by carrying out the synthesis in the same manner as in Preparation Example 1.

[0374] [Table 1]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384] Preparation Example 2. Preparation of Compound 1-467

[0385]

[0386] After dissolving 10.0 g (16.2 mmol / L) of Compound 1-135 in d6-benzene (100 mL) in a 250 mL two-necked flask, 9.7 mL (110.2 mmol / L) of trifluoromethanesulfonic acid was slowly added thereto, and then the resulting solution was refluxed. After completion of the reaction, the resulting product was purified by recrystallization using methanol, and 9.9 g (95.1%) of the target compound 1-467 was obtained.

[0387] Except for using Intermediate A in Table 2 below instead of Compound 1-135 in Preparation Example 2, the target compounds in Table 2 below were synthesized by carrying out the synthesis in the same manner as in Preparation Example 2.

[0388] [Table 2]

[0389]

[0390]

[0391]

[0392]

[0393] Preparation Example 3. Preparation of Compound 3-4

[0394]

[0395] Preparation Example 3-1. Preparation of Compound 3-1-4

[0396] In a 1-L two-necked flask, 30.0 g (90.5 mmol / L) of Compound 2-3-737, 12.1 g (99.6 mmol / L) of phenylboronic acid, 5.2 g (4.5 mmol / L) of Pd(PPh3)4, and 25.0 g (181.0 mmol / L) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL), and then the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 24.8 g (83.3%) of the target compound 3-1-4 was obtained.

[0397] Preparation Example 3-2. Preparation of Compound 3-4

[0398] 10.0 g (30.4 mmol / L) of Compound 3-1-4, 11.3 g (30.4 mmol / L) of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, 1.4 g (1.5 mmol / L) of Pd2dba3, 1.4 g (3.0 mmol / L) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), and 5.8 g (60.8 mmol / L) of NaOtBu were placed in a 250-mL two-necked flask and dissolved in toluene (150 mL). Then, the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 17.6 g (87.2%) of the target compound 3-4 was obtained.

[0399] Except that Intermediate A in Table 3 below was used instead of phenylboronic acid and Intermediate B in Table 3 below was used instead of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine in Preparation Example 3, the target compounds in Table 3 below were synthesized by performing the synthesis in the same manner as in Preparation Example 3.

[0400] [Table 3]

[0401]

[0402]

[0403]

[0404] Preparation Example 4. Preparation of Compound 3-103

[0405]

[0406] In a 250 mL two-necked flask, 10.0 g (30.4 mmol / L) of Compound 3-1-4, 11.1 g (30.4 mmol / L) of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid, 1.4 g (1.5 mmol / L) of Pd2dba3, 1.4 g (3.0 mmol / L) of Xphos, and 8.4 g (60.8 mmol / L) of K2CO3 were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL). After that, the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 15.1 g (80.9%) of the target compound 3-103 was obtained.

[0407] Except that Intermediate A in Table 4 below was used instead of phenylboronic acid in Preparation Example 3 and Intermediate B in Table 4 below was used instead of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid in Preparation Example 4, the target compounds in Table 4 below were synthesized by conducting the synthesis in the same manner as in Preparation Example 3 and Preparation Example 4.

[0408] [Table 4]

[0409]

[0410]

[0411] Preparation Example 5. Preparation of Compound 3-191

[0412]

[0413] Preparation Example 5-1. Preparation of Compound 3-2-191

[0414] In a 1 L two-necked flask, 30.0 g (118.7 mmol / L) of 7-chloronaphtho[1,2-b]benzofuran, 15.9 g (130.6 mmol / L) of phenylboronic acid, 5.4 g (5.9 mmol / L) of Pd2dba3, 5.7 g (11.9 mmol / L) of Xphos, and 9.5 g (237.4 mmol / L) of NaOH were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL). After that, the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 31.5 g (90.1%) of the target compound 3-2-191 was obtained.

[0415] Preparation Example 5-2. Preparation of Compound 3-1-191

[0416] In a 1 L two-necked flask, 31.0 g (105.3 mmol / L) of compound 3-2-191 and 18.7 g (105.3 mmol / L) of N-bromosuccinimide were dissolved in dimethyl formamide (DMF) (300 mL). After that, the resulting solution was refluxed. After the reaction was completed, the resulting product was purified by recrystallization using methanol, and 34.5 g (87.7%) of the target compound 3-1-191 was obtained.

[0417] Preparation Example 5-3. Preparation of Compound 3-191

[0418] In a 250 mL two-necked flask, 10.0 g (26.8 mmol / L) of compound 3-1-191, 11.8 g (26.8 mmol / L) of (4-([1,1':4',1”-terphenyl]-4-yl(phenyl)amino)phenyl)boronic acid, 1.2 g (1.3 mmol / L) of Pd2dba3, 1.3 g (2.7 mmol / L) of Xphos, and 7.4 g (53.6 mmol / L) of K2CO3 were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL). After that, the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 16.1 g (86.9%) of the target compound 3-191 was obtained.

[0419] Except for using Intermediate A in Table 5 below instead of phenylboronic acid and using Intermediate B in Table 5 below instead of (4-([1,1':4',1”-terphenyl]-4-yl(phenyl)amino)phenyl)boronic acid in Preparation Example 5, the target compounds in Table 5 below were synthesized by performing the synthesis in the same manner as in Preparation Example 5.

[0420] [Table 5]

[0421]

[0422] Preparation Example 6. Preparation of Compound 3-139

[0423]

[0424] In a 250 mL two-necked flask, 10.0 g (26.8 mmol / L) of Compound 3-1-191, 8.6 g (26.8 mmol / L) of N-phenyl-[1,1':4',1”-terphenyl]-4-amine, 1.2 g (1.3 mmol / L) of Pd2dba3, 1.3 g (2.7 mmol / L) of Xphos, and 5.2 g (53.6 mmol / L) of NaOtBu were dissolved in 100 mL of toluene. After that, the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization using methanol, and 14.1 g (85.8%) of the target compound 3-139 was obtained.

[0425] Except for using Intermediate A in Table 6 below instead of phenylboronic acid in Preparation Example 3 and using Intermediate B in Table 6 below instead of N-phenyl-[1,1':4',1”-terphenyl]-4-amine in Preparation Example 6, the target compounds in Table 6 below were synthesized by carrying out the synthesis in the same manner as in Preparation Example 6.

[0426] [Table 6]

[0427]

[0428]

[0429] Other compounds other than those described in Preparation Examples 1 to 6 and Tables 1 to 6 were also prepared in the same manner as in the above Preparation Examples, and the synthesis results are shown in Tables 7 and 8 below. Table 7 below shows the measured values of 1H nuclear magnetic resonance (NMR) (CDCl3, 400 MHz), and Table 8 below shows the measured values of field desorption mass spectrometry (FD-MS).

[0430] [Table 7]

[0431]

[0432]

[0433] [Table 8]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444] <Example 1>

[0445] 1) Fabrication of Organic Light-Emitting Device (Red Host)

[0446] The glass substrate on which ITO was thinly coated to a thickness of 1,500 Å was ultrasonically washed with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically washed with solvents (such as acetone, methanol, and isopropyl alcohol), dried, and then subjected to ultraviolet ozone (UVO) treatment for 5 minutes using UV in an ultraviolet (UV) cleaning machine. After that, the substrate was transferred to a plasma washing machine (plasma treatment (PT)), and then subjected to plasma treatment under a vacuum state for ITO surface treatment and removal of the residual film, and the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0447] As a common layer, a hole injection layer of 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer of N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1”-biphenyl)-4,4'-diamine (NPB) were formed on the ITO transparent electrode (positive electrode).

[0448] As described below, a light-emitting layer was thermally vacuum-deposited thereon. A light-emitting layer with a thickness of 400 Å was deposited by depositing one or both of the compounds set forth in Table 9 below from a single source as a red host and doping the host with an Ir compound in an amount of 3 wt% using (piq)2(Ir)(acac) as a red phosphorescent dopant. Thereafter, bathophenanthroline (Bphen) with a thickness of 30 Å was deposited as a hole-blocking layer, and Alq3 with a thickness of 250 Å was deposited thereon as an electron-transporting layer. Finally, lithium fluoride (LiF) with a thickness of 10 Å was deposited on the electron-transporting layer to form an electron-injecting layer, and then aluminum (Al) with a thickness of 1,200 Å was deposited on the electron-injecting layer to form a negative electrode, thereby fabricating an organic electroluminescent device.

[0449] In this case, Comparative Compounds A to R used in Comparative Examples 1 to 15 and Comparative Examples 25 to 38 are as follows.

[0450]

[0451] 2) Driving voltage and luminous efficiency of the organic electroluminescent device

[0452] For the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured by M7000 manufactured by McScience Inc., and based on the measurement results, T95 at a reference brightness of 6,000 candela / m² was measured by a service life measurement device (M6000) manufactured by McScience Inc. As described above, T95 means the service life (unit: hours) of the device measured when the brightness reaches 95% of the initial brightness.

[0453] Table 9 below shows experimental examples or comparative examples in which the compounds of Chemical Formula 1 and Chemical Formula 2 of the present invention are used as host materials for the light-emitting layer.

[0454] [Table 9]

[0455]

[0456]

[0457]

[0458] In Table 9, the ratio (N:P) means the weight ratio of the N-type host to the P-type host. For example, the N-type host corresponds to the compound of Chemical Formula 1 of the present application, and the P-type host corresponds to the compound of Chemical Formula 2 of the present application.

[0459] In Table 9, "Turn-on" (V) means the voltage required to generate 1 nit of luminance.

[0460] As can be seen in Table 9, it can be confirmed that in the case of an organic light-emitting device in which the organic material layer contains the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 of the present invention, compared with the comparative examples, the driving voltage, luminous efficiency, and service life are excellent.

[0461] This indicates that when the compound of Chemical Formula 1, which is an acceptor (n-type host) having good electron-transporting ability, and the compound of Chemical Formula 2, which is a donor (p-type host) having good hole-transporting ability, are used as co-hosts of the light-emitting layer, the driving voltage can be reduced because electrons and holes are smoothly injected into the light-emitting layer, and the efficiency and service life of the device are improved by forming an effective recombination region.

[0462] In particular, as shown in Comparative Examples 25 to 38 in Table 9, it can be confirmed that when two types of compounds are used as materials for the light-emitting layer, but only either the compound of Chemical Formula 1 or the compound of Chemical Formula 2 of the present application is used, the efficiency and service life of the device are inferior to those of the devices in the examples.

[0463] When only the compound of Chemical Formula 1 having good electron-transporting ability is present in the light-emitting layer, electrons entering from the electron-transporting layer accumulate at the interface between the light-emitting layer and the hole-transporting layer, resulting in deterioration at the interface, thereby reducing the efficiency and service life.

[0464] When only the compound of Chemical Formula 2 having good hole-transporting ability is present in the light-emitting layer, it is difficult to inject electrons into the light-emitting layer, and deterioration occurs at the interface between the light-emitting layer and the electron-transporting layer, thereby reducing the efficiency and service life.

[0465] <Experimental Example 2>

[0466] 1) Fabrication of an organic light-emitting device (red host)

[0467] The glass substrate on which ITO was thinly coated to a thickness of 1,500 Å was ultrasonically washed with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically washed with solvents (such as acetone, methanol, and isopropyl alcohol), dried, and then subjected to UVO treatment for 5 minutes using UV in a UV cleaning machine. After that, the substrate was transferred to a plasma washing machine (PT), and then subjected to plasma treatment in a vacuum state to achieve the ITO work function and remove the residual film, and the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0468] As a common layer, a hole injection layer of 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer of N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) were formed on the ITO transparent electrode (positive electrode).

[0469] As described below, a light-emitting layer was thermally vacuum-deposited thereon. A light-emitting layer with a thickness of 400 Å was deposited by depositing one or both of the compounds set forth in Table 10 below from a single supply source as a red host and doping the host with the Ir compound in an amount of 3 wt% using (piq)2(Ir)(acac) as a red phosphorescent dopant. Thereafter, Bphen with a thickness of 30 Å was deposited as a hole-blocking layer, and 2,2',2”-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBI) with a thickness of 250 Å was deposited thereon as an electron transport layer. Finally, lithium fluoride (LiF) with a thickness of 10 Å was deposited on the electron transport layer to form an electron injection layer, and then aluminum (Al) with a thickness of 1,200 Å was deposited on the electron injection layer to form a negative electrode, thereby manufacturing an organic electroluminescent element.

[0470] 2) Driving voltage and luminous efficiency of the organic electroluminescent element

[0471] For the organic electroluminescent element manufactured as described above, the electroluminescence (EL) characteristics were measured by M7000 manufactured by Mike Science Co., Ltd., and based on the measurement results, T95 was measured by a service life measurement device (M6000) manufactured by Mike Science Co., Ltd. when the reference luminance was 6,000 candela / m². As described above, T95 means the service life (unit: hours) of the element measured when the luminance reaches 95% of the initial luminance.

[0472] Table 10 below shows experimental examples or comparative examples in which the compounds of Chemical Formula 1 and Chemical Formula 2 of the present invention are used as host materials for the light-emitting layer.

[0473] [Table 10]

[0474]

[0475] Experimental Example 2 is an experiment in which an electron-blocking layer is additionally included in the organic material layer, and when the electron-blocking layer is inserted in the middle, the effect is excellent because the recombination of holes and electrons is effectively formed by effectively preventing electrons from moving to the common layer to confine electrons inside the light-emitting layer.

[0476] That is, it can be confirmed that the service life is improved because electrons are effectively formed in the light-emitting layer to improve charge balance.

Claims

1. An organic light-emitting element, comprising: The first electrode; The second electrode; And an organic material layer disposed between the first electrode and the second electrode, Wherein the organic material layer comprises a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2: [Chemical Formula 1] In Chemical Formula 1, X is O or S, L1 and L2 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene, Z1 is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, N - Het is a substituted or unsubstituted monocyclic or polycyclic C2 - C60 heteroaryl including one or more Ns, R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, a and b are each an integer from 0 to 3, and when a is 2 or greater than 2, L1s are the same as or different from each other, and when b is 2 or greater than 2, L2s are the same as or different from each other, p and t1 are each an integer from 1 to 3, and when p is 2 or greater than 2, Z1s are the same as or different from each other, and when t1 is 2 or greater than 2, N - Hets are the same as or different from each other, [Chemical Formula 2] In Chemical Formula 2, L3 and L4 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted C6 - C60 arylene, Z2 and Z3 are each independently a substituted or unsubstituted amino group; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, Either one of Z2 and Z3 is a substituted or unsubstituted amino group, and the other is a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, R7 and R8 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, c and d are each an integer from 0 to 3, and when c is 2 or greater than 2, L3s are the same as or different from each other, and when d is 2 or greater than 2, L4s are the same as or different from each other, p2 and p3 are each an integer from 1 to 3, and when p2 is 2 or greater than 2, Z2s are the same as or different from each other, and when p3 is 2 or greater than 2, Z3s are the same as or different from each other, r is an integer from 0 to 5, and when r is 2 or greater than 2, R7s are the same as or different from each other, and s is an integer from 0 to 3, and when s is 2 or greater than 2, R8s are the same as or different from each other.

2. The organic light-emitting element according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 1-1 and Chemical Formula 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In Chemical Formula 1-1 and Chemical Formula 1-2, X, R1 to R6, L1, L2, Z1, N-Het, a, b, p and t1 are the same as defined in Chemical Formula 1.

3. The organic light-emitting element according to claim 1, wherein the N-Het is represented by the following Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, and X5 is CR15 or N, at least one of X1 to X5 is N, and R11 to R15 are the same as or different from each other, and each independently is selected from the group consisting of: hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and an amino group substituted with an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

4. The organic light-emitting device according to claim 3, wherein Chemical Formula 3 is represented by any one of the following Chemical Formula 3-1 to Chemical Formula 3-3: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] In Chemical Formula 3-1 to Chemical Formula 3-3, X6 to X9 are each N or CR16, at least one of X6 to X8 is N, A and B are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl ring; or a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic ring, and R16 and R61 to R64 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

5. The organic light-emitting device according to claim 1, wherein Z1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted benzo[ghi]perylenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphtho[2,3-b]benzofuranyl group; a substituted or unsubstituted naphtho[2,3-b]benzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

6. The organic light-emitting element according to claim 1, wherein the deuterium content of the compound of Chemical Formula 1 is 0% or 1% to 100%.

7. The organic light-emitting element according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

8. The organic light-emitting element according to claim 1, wherein Chemical Formula 2 is represented by Chemical Formula 2-1 or Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In Chemical Formula 2-1 and Chemical Formula 2-2, L3, L4, R7, R8, c, d, r, and s are the same as defined in Chemical Formula 2, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, Z4 and Z5 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, and p4 and p5 are each an integer from 1 to 3, and when p4 is 2 or greater than 2, Z4 are the same as or different from each other, and when p5 is 2 or greater than 2, Z5 are the same as or different from each other.

9. The organic light - emitting element according to claim 1, wherein Z2 and Z3 are the same as or different from each other, and each independently is an amino group substituted by a substituted or unsubstituted C6 - C60 aryl group or a substituted or unsubstituted C2 - C60 heteroaryl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and either one of Z2 and Z3 is an amino group substituted by a substituted or unsubstituted C6 - C60 aryl group or a substituted or unsubstituted C2 - C60 heteroaryl group, and the other is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

10. The organic light - emitting element according to claim 8, wherein Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzofuranyl group; or a substituted or unsubstituted naphthobenzothiophenyl group.

11. The organic light - emitting element according to claim 1, wherein the deuterium content of the compound of Formula 2 is 0% or 1% to 100%.

12. The organic light - emitting element according to claim 1, wherein Formula 2 is represented by any one of the following compounds:

13. The organic light-emitting element according to claim 1, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound of Chemical Formula 1 and the compound of Chemical Formula 2.

14. The organic light-emitting element according to claim 1, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains a host material, and the host material includes the compound of Chemical Formula 1 and the compound of Chemical Formula 2.

15. The organic light-emitting element according to claim 1, further comprising one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

16. A composition for forming an organic material layer, comprising the compound of the following Chemical Formula 1 and the compound of the following Chemical Formula 2: [Chemical Formula 1] In Chemical Formula 1, X is O or S, L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene, Z1 is a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, N-Het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heteroaryl including one or more Ns, R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, a and b are each an integer from 0 to 3, and when a is 2 or more than 2, L1s are the same as or different from each other, and when b is 2 or more than 2, L2s are the same as or different from each other, p and t1 are each an integer from 1 to 3, and when p is 2 or more than 2, Z1s are the same as or different from each other, and when t1 is 2 or more than 2, N-Hets are the same as or different from each other, [Chemical Formula 2] In Chemical Formula 2, L3 and L4 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, Z2 and Z3 are each independently a substituted or unsubstituted amino group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Either of Z2 and Z3 is a substituted or unsubstituted amino group, and the other is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R7 and R8 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, c and d are each an integer from 0 to 3, and when c is 2 or greater, L3 are the same as or different from each other, and when d is 2 or greater, L4 are the same as or different from each other, p2 and p3 are each an integer from 1 to 3, and when p2 is 2 or greater, Z2 are the same as or different from each other, and when p3 is 2 or greater, Z3 are the same as or different from each other, r is an integer from 0 to 5, and when r is 2 or greater, R7 are the same as or different from each other, and s is an integer from 0 to 3, and when s is 2 or greater, R8 are the same as or different from each other.

17. The composition according to claim 16, wherein the weight ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 is 1:10 to 10:1.

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