Heterocyclic compound, organic light-emitting device including same, and composition for organic layer of organic light-emitting device

Abstract

The present disclosure relates to a heterocyclic compound represented by the following formula, an organic light-emitting device including the heterocyclic compound, and an organic light-emitting display device including the organic light-emitting device. An organic heterocyclic ring is included in an organic material layer of the organic light-emitting device. # imgabs0 #

Description

[0001] This application is a divisional application of an invention patent application with an application date of April 15, 2022, application number 202210400119.2, and invention name “Heterocyclic compounds, organic light-emitting devices including the heterocyclic compounds, and compositions of organic layers for organic light-emitting devices”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims the benefit of Korean Patent Application No. 10-2021-0049748 filed in Korea on April 16, 2021, and Korean Patent Application No. 10-2021-0194155 filed in Korea on December 31, 2021, all of which are incorporated herein by reference in their entirety. Technical Field

[0004] The present disclosure relates to heterocyclic compounds, and more particularly, to heterocyclic compounds, organic light-emitting devices including the heterocyclic compounds, and compositions for organic layers of the organic light-emitting devices. Background Art

[0005] An organic light emitting display device, which may be called an electroluminescent display device, is a self-luminous display device and has the advantages of a wide viewing angle, good contrast, and fast response speed.

[0006] The 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, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may have a single-layer structure or a multi-layer structure.

[0007] The material of the organic film may have a light-emitting function. For example, a single compound may be used for the organic film. Alternatively, a compound used as a host and a compound used as a dopant may be used for the organic film in a host-guest system. In addition, as the material of the organic film, a compound that can play the role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may be used.

[0008] In order to improve the performance, lifespan or efficiency of organic light-emitting devices, there is a continuous need to develop materials for organic thin films.

[0009] There is a need to study a chemical structure that can satisfy conditions required for a material that can be used for an organic light-emitting device, such as a suitable energy level, electrochemical stability, and thermal stability, and can play various roles required in an organic light-emitting device according to a substituent. Summary of the invention

[0010] Embodiments of the present disclosure are directed to heterocyclic compounds, organic light-emitting devices, and compositions for organic layers of organic light-emitting devices that substantially obviate one or more problems associated with limitations and disadvantages of the related art.

[0011] The additional features and advantages of the present disclosure are set forth in the following description, which will become apparent from the specification or may be clarified through the practice of the present disclosure. The purpose and other advantages of the present disclosure are realized and obtained through the features described herein and in the accompanying drawings.

[0012] To achieve these and other advantages for the purpose of embodiments according to the present disclosure, as described herein, one aspect of the present disclosure is a heterocyclic compound of Formula 1:

[0013] [Formula 1]

[0014]

[0015] wherein N-Het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group having at least one nitrogen atom, wherein L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C60 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroarylene group, and a is an integer from 1 to 3, wherein when a is 2 or more, two or more L are the same or different, wherein R1 to R12 are the same or different, wherein each of R1 to R12 is one is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl; deuterated or undeuterated substituted or unsubstituted C2 R1 to R12 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring, wherein b is an integer from 1 to 3. , wherein when b is 2 or greater, two or more R9 are the same or different, wherein R, R' and R" are the same or different, wherein each of R, R' and R" is independently selected from the group consisting of deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; or deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, and wherein the deuteration rate of the heterocyclic compound is 20% to 100%.

[0016] Another aspect of the present disclosure is an organic light-emitting device, comprising a first electrode; a second electrode facing the first electrode; and at least one organic material layer between the first electrode and the second electrode, wherein one or more of the at least one organic material layer comprises a first compound that is the above-mentioned heterocyclic compound.

[0017] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the disclosure as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure.

[0019] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure.

[0020] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure.

[0021] Figure 3 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure.

[0022] Figure 4 It is a schematic diagram illustrating the exciplex phenomenon.

[0023] Figure 5 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure.

[0024] Figure 6 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure.

[0025] Figure 7 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure.

[0026] Figure 8 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure.

[0027] Fig. 9 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0028] Reference will now be made in detail to some examples and preferred embodiments which are illustrated in the accompanying drawings.

[0029] In an exemplary embodiment of the present disclosure, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2. The element symbol of deuterium may be D or 2H.

[0030] In the exemplary embodiment of the present disclosure, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0031] In the exemplary embodiment of the present disclosure, the content T% of the specific substituent is defined as T2 / T1*100. T1 is the total number of substituents, and T2 is the number of the specific substituents.

[0032] For example, when When one of the five possible substituents (T1) in the phenyl group represented by is substituted by deuterium, The deuterium content in the phenyl group represented can be expressed as 20%.

[0033] In this specification, the deuteration rate (e.g., deuterium rate) refers to the ratio of hydrogen in a compound that is replaced by deuterium. That is, if a compound contains "a" hydrogens and "b" deuteriums, the deuteration rate can be calculated as b*100 / (a+b). In this specification, the deuteration rate can be referred to as the deuterium content.

[0034] In this specification, a phenyl group with a deuteration rate of 20% can be represented as follows:

[0035]

[0036] In the present specification, a phenyl group having a deuteration rate of 0% may be a phenyl group having no deuterium, that is, 5 hydrogen atoms.

[0037] In the present specification, halogen may include fluorine, chlorine, bromine and iodine.

[0038] In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be substituted. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. For example, the alkyl group may 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, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0039] In this specification, alkenyl includes straight or branched chains with 2 to 60 carbon atoms, and may be substituted. The carbon number of alkenyl may be 2 to 60, specifically 2 to 40, more specifically 2 to 20. For example, alkenyl may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styryl and the like, but are not limited thereto.

[0040] In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be substituted. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0041] In this specification, alkoxy can be straight chain, branched chain or cyclic chain. Although the carbon number of alkoxy is not specifically limited, it is preferred that the carbon number of alkoxy is 1 to 20. For example, alkoxy may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

[0042] In this specification, cycloalkyl includes monocyclic or polycyclic rings with 3 to 60 carbon atoms, and may be substituted. Here, polycyclic refers to a group formed by direct connection or condensation of cycloalkyl and other cyclic groups, and the cyclic group may be a cycloalkyl, a heterocycloalkyl, an aryl, a heteroaryl or the like. Cycloalkyl may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. For example, cycloalkyl may 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 the like, but is not limited thereto.

[0043] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms and can be monocyclic or polycyclic with 2 to 60 carbon atoms. Heterocycloalkyl can be substituted. Here, polycyclic refers to a group formed by direct connection or condensation of heterocycloalkyl with other cyclic groups, and the cyclic group can be heterocycloalkyl, cycloalkyl, aryl, heteroaryl or the like. Heterocycloalkyl can have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0044] In the present specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be substituted. Here, polycyclic refers to a group formed by direct connection or condensation of aryl with other cyclic groups, and the cyclic groups may be aryl, cycloalkyl, heterocycloalkyl, heteroaryl or the like. The number of carbon atoms of aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. For example, aryl may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, The invention also includes, but is not limited to, a chrysenyl group, a phenanthrenyl group, a peryl group, a fluoranthenyl group, a triphenyl group, a phenalenyl group, a pyrenyl group, a tetraphenyl group, a pentacene group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, a condensed ring group thereof, and the like.

[0045] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined (connected or linked) with each other to form a ring. That is, the substituted fluorenyl group may include a spirofluorenyl group.

[0046] The substituted fluorenyl group may be represented by the following, but is not limited thereto.

[0047]

[0048] In this specification, heteroaryl includes O, S, Se, N or Si as heteroatoms and can be monocyclic or polycyclic with 2 to 60 carbon atoms. Heteroaryl can be substituted. Here, polycyclic refers to the group formed by direct connection or condensation of heteroaryl and other cyclic groups, and the cyclic group can be heteroaryl, cycloalkyl, heterocyclic radical, aryl or the like. Heteroaryl can have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. For example, heteroaryl can include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl (furazanyl group), oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl (dioxynyl group), triazine, tetrazine, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinazolyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthazinyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilolyl (dibenzosilol group), dihydrophenazinyl, phenoxazinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, panazinyl, phenothiazinyl, phthalazinyl, decalinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilanyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indolazolyl, pyrido[1,2-a]imidazo[1,2-e]indolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, and the like, but are not limited thereto.

[0049] In the present specification, the amine group is selected from the group consisting of monoalkylamine, monoarylamine, monoheteroarylamine, -NH 2 The amine group may be a group consisting of a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, an aniline group, a naphthylamine group, a benzylamine group, a diphenylamine group, an anthracenamine group, a 9-methyl-anthracenamine group, a diphenylamine group, a ditolylamine group, a phenyltoluidine group, a triphenylamine group, a diphenylnaphthylamine group, a phenylbenzidine group, a diphenylfluoreneamine group, a phenyltriphenylamine group, a diphenyltriphenylamine group and the like, but is not limited thereto.

[0050] In this specification, arylene means that an aryl group has two bonding positions, i.e., a divalent group. Except that each of these groups is a divalent group, the above description of aryl groups can be applied. In addition, heteroarylene means that a heteroaryl group has two bonding positions, i.e., a divalent group. Except that each of these groups is a divalent group, the above description of heteroaryl groups can be applied.

[0051] In this specification, the phosphine oxide group is represented by -P(=O)R 101 R 102 Indicates. 101 and R 102 Same or different, R 101 and R 102 Each of is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic groups. The phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but is not limited thereto.

[0052] In this specification, a silyl group is a substituent including a Si atom, which is directly attached as a radical and is represented by -SiR 104 R 105 R 106 Indicates. 104 To R 106 Same or different, R 104 To R 106 Each of is independently selected from hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl and heterocyclic. The silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0053] As used herein, "adjacent" groups may refer to a pair of a substituent substituted on one atom and another substituent substituted on another atom directly connected to the atom, a pair of a substituent and another substituent closest to the atom in space, and a pair of a substituent and another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position of a benzene ring and two substituents substituted on the same carbon of an aliphatic ring may be interpreted as "adjacent" groups.

[0054] The aliphatic or aromatic hydrocarbon ring or heterocyclic ring formed by adjacent groups may have the structures exemplified by the above-mentioned cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group, except that the aliphatic or aromatic hydrocarbon ring or heterocyclic ring that may be formed by adjacent groups is not a monovalent group.

[0055] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is located (i.e., the position where the substituent can be substituted) is substituted. When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0056] In the present specification, "substituted" means that at least one hydrogen in the compound is substituted by at least one selected from the group consisting of the following groups or by a substituent formed by at least two groups: deuterium; C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P (=O)RR';C1 to C20 alkylamine;C6 to C60 monocyclic or polycyclic arylamine;And C2 to C60 monocyclic or polycyclic heteroarylamine. In this case, each of R, R' and R" may be the same or different, and each of R, R' and R" may be independently selected from the group consisting of: deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl.

[0057] The heterocyclic compound of the present disclosure is represented by Formula 1.

[0058] [Formula 1]

[0059]

[0060] In Formula 1, "N-Het" is a deuterated or undeuterated, substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group having (or including) at least one nitrogen atom (N).

[0061] L is a direct bond (single bond), a deuterated or undeuterated substituted or unsubstituted C6 to C60 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroarylene group, and a is an integer of 1 to 3. When a is 2 or more, two or more L are the same or different.

[0062] R1 to R12 are the same or different. Each of R1 to R12 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycloalkane; R1 to R12 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring. b is an integer from 1 to 3. When b is 2 or more, two or more R9 are the same or different.

[0063] R, R' and R" are the same or different, and each of R, R' and R" is independently selected from the group consisting of deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; or deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl.

[0064] For example, the heterocyclic compound of Formula 1 may have a deuteration rate of 20% to 100%.

[0065] In an exemplary embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be represented by one of Formulae 3 to 6.

[0066] [Formula 3]

[0067]

[0068] [Formula 4]

[0069]

[0070] [Formula 5]

[0071]

[0072] [Formula 6]

[0073]

[0074] In Formulae 3 to 6, the definitions of N—Het, R1 to R12, L, a, and b are the same as those in Formula 1.

[0075] In an exemplary embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be represented by one of Formula 7 and Formula 8.

[0076] [Formula 7]

[0077]

[0078] [Formula 8]

[0079]

[0080] In Formulae 7 and 8, the definitions of N—Het, R1 to R12, L, a and b are the same as those in Formula 1.

[0081] In the exemplary embodiment of the present disclosure, R9 to R12 may be the same or different. Each of R9 to R12 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more R9 to R12 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0082] In the exemplary embodiment of the present disclosure, R9 to R12 may be the same or different. Each of R9 to R12 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C40 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroaryl, or two or more R9 to R12 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C40 aromatic ring or a deuterated or undeuterated substituted or unsubstituted C2 to C40 heterocycle.

[0083] In the exemplary embodiment of the present disclosure, R9 to R12 may be the same or different, and each of R9 to R12 may be independently selected from the group consisting of hydrogen and deuterium.

[0084] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C60 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroarylene group.

[0085] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C40 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroarylene group.

[0086] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C30 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C30 heteroarylene group.

[0087] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C20 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C20 heteroarylene group.

[0088] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated C6 to C20 arylene group, or a deuterated or undeuterated C2 to C20 heteroarylene group.

[0089] In an exemplary embodiment of the present disclosure, L is a direct bond, or a deuterated or undeuterated monocyclic or polycyclic C6 to C20 arylene group.

[0090] In an exemplary embodiment of the present disclosure, L is a direct bond, a deuterated or undeuterated phenylene group, a deuterated or undeuterated biphenylene group, or a deuterated or undeuterated naphthylene group.

[0091] In an exemplary embodiment of the present disclosure, “N-Het” is a substituted or unsubstituted, deuterated or undeuterated monocyclic or polycyclic C2 to C60 heterocyclic group having (or including) at least one nitrogen atom (N).

[0092] In an exemplary embodiment of the present disclosure, “N-Het” is a substituted or unsubstituted deuterated or undeuterated monocyclic or polycyclic C2 to C40 heterocyclic group having (or including) at least one nitrogen atom (N).

[0093] In an exemplary embodiment of the present disclosure, “N-Het” is a substituted or unsubstituted, deuterated or undeuterated monocyclic or polycyclic C2 to C20 heterocyclic group having (or including) at least one nitrogen atom (N).

[0094] In an exemplary embodiment of the present disclosure, "N-Het" is substituted with at least one substituent selected from the group consisting of deuterium, a deuterated or undeuterated C1 to C20 alkyl group, a deuterated or undeuterated C6 to C20 aryl group, and a deuterated or undeuterated C2 to C20 heteroaryl group, and is a deuterated or undeuterated monocyclic or polycyclic C2 to C20 heterocyclic group having (or including) at least one nitrogen atom (N).

[0095] In an exemplary embodiment of the present disclosure, N-Het may be a deuterated or undeuterated substituted or unsubstituted pyridyl group; a deuterated or undeuterated substituted or unsubstituted pyrimidinyl group; a deuterated or undeuterated substituted or unsubstituted triazinyl group; a deuterated or undeuterated substituted or unsubstituted quinolyl group; a deuterated or undeuterated substituted or unsubstituted isoquinolyl group; a deuterated or undeuterated substituted or unsubstituted benzimidazolyl group; or a deuterated or undeuterated substituted or unsubstituted phenanthroline group.

[0096] In an exemplary embodiment of the present disclosure, N-Het may be represented by one of the structures in Formula 1a:

[0097] [Formula 1a]

[0098]

[0099] In Formula 1a, R21 to R25 are the same or different. Each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C R21 to R25 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C2 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring. R is selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycloalkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl.

[0100] In an exemplary embodiment of the present disclosure, R21 to R25 are the same or different. Each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more R21 to R25 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0101] In an exemplary embodiment of the present disclosure, R21 to R25 are the same or different, and each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl.

[0102] In an exemplary embodiment of the present disclosure, R21 to R25 are the same or different, and each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C40 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroaryl.

[0103] In an exemplary embodiment of the present disclosure, R21 to R25 are the same or different, and each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; C1 to C40 alkyl unsubstituted or substituted with deuterium; C6 to C40 aryl unsubstituted or substituted with deuterium or C1 to C20 alkyl; and C2 to C40 heteroaryl unsubstituted or substituted with deuterium.

[0104] In an exemplary embodiment of the present disclosure, R21 to R25 are the same or different, and each of R21 to R25 is independently selected from the group consisting of: hydrogen; deuterium; unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted biphenyl; unsubstituted or deuterium-substituted dimethyl-fluorenyl; unsubstituted or deuterium-substituted dibenzofuran; and unsubstituted or deuterium-substituted dibenzothiophene.

[0105] In an exemplary embodiment of the present disclosure, R1 to R8 in Formula 1 are the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl; deuterated or undeuterated R1 to R8 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C2 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0106] In the exemplary embodiment of the present disclosure, R1 to R8 may be the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more R1 to R8 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0107] In the exemplary embodiment of the present disclosure, R1 to R8 may be the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more R1 to R8 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycle.

[0108] In the exemplary embodiment of the present disclosure, R1 to R8 may be the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or non-deuterated substituted or unsubstituted C6 to C40 aryl; and deuterated or non-deuterated substituted or unsubstituted C2 to C40 heteroaryl, or two or more R1 to R8 may be bonded to each other to form a deuterated or non-deuterated substituted or unsubstituted C6 to C40 aromatic ring or a deuterated or non-deuterated substituted or unsubstituted C2 to C40 heterocycle.

[0109] In the exemplary embodiment of the present disclosure, R1 to R8 may be the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; C6 to C40 aryl groups that are not substituted or substituted with deuterium; and C2 to C40 heteroaryl groups that are not substituted or substituted with deuterium, or two or more R1 to R8 may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring that is not substituted or substituted with deuterium or C6 to C40 aryl groups, or a C2 to C40 heterocyclic ring that is not substituted or substituted with deuterium or C6 to C40 aryl groups.

[0110] In the exemplary embodiment of the present disclosure, R1 to R8 may be the same or different. Each of R1 to R8 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted phenyl; and deuterated or undeuterated substituted or unsubstituted dibenzothiophene, or two or more R1 to R8 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted indole ring; a deuterated or undeuterated substituted or unsubstituted indene ring; a deuterated or undeuterated substituted or unsubstituted benzofuran ring; or a deuterated or undeuterated substituted or unsubstituted benzothiophene ring.

[0111] In an exemplary embodiment of the present disclosure, It can be expressed by equation 9 or 10, and It is the position of bonding to the dibenzofuran structure.

[0112] [Formula 9]

[0113]

[0114] [Formula 10]

[0115]

[0116] In Formula 9 and Formula 10, the definitions of R1 to R4 are the same as those in Formula 1, and Y is O, S, NRb, or CRbRb'.

[0117] Each of R41 to R48 is independently selected from the group consisting of hydrogen, deuterium, a deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl group, and a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl group.

[0118] Rb, Rb', R31 and R32 are the same or different. Each of Rb, Rb', R31 and R32 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C Rb, Rb', R31 and R32 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C2 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring. f is an integer from 0 to 4. When f is 2 or more, R31 is the same or different. g is an integer from 0 to 2. When f is 2, R32 is the same or different.

[0119] In an exemplary embodiment of the present disclosure, the structure of Formula 9 may be represented by one of the structures in Formula 9a.

[0120] [Formula 9a]

[0121]

[0122] In Formula 9a, the definitions of the substituents are the same as those in Formula 9.

[0123] In an exemplary embodiment of the present disclosure, R31 and R32 may be the same as each other, and each of R31 and R32 may be independently selected from hydrogen and deuterium.

[0124] In an exemplary embodiment of the present disclosure, Rb and Rb′ may be identical to each other, and each of Rb and Rb′ may be selected from the group consisting of hydrogen, deuterium, deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl, and deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl.

[0125] In an exemplary embodiment of the present disclosure, Rb and Rb′ may be identical to each other, and each of Rb and Rb′ may be selected from the group consisting of hydrogen, deuterium, deuterated or undeuterated substituted or unsubstituted C1 to C40 alkyl, and deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl.

[0126] In an exemplary embodiment of the present disclosure, Rb and Rb′ may be identical to each other, and each of Rb and Rb′ may be selected from the group consisting of hydrogen, deuterium, a C1 to C40 alkyl group which is unsubstituted or substituted with deuterium, and a C6 to C40 aryl group which is unsubstituted or substituted with deuterium.

[0127] In an exemplary embodiment of the present disclosure, Rb and Rb′ may be identical to each other, and each of Rb and Rb′ may be selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1 to C20 alkyl, and unsubstituted or deuterium-substituted C6 to C20 aryl.

[0128] In the exemplary embodiment of the present disclosure, Rb and Rb′ may be identical to each other, and each of Rb and Rb′ may be selected from the group consisting of hydrogen, deuterium, a phenyl group which is unsubstituted or substituted with deuterium, and a methyl group which is unsubstituted or substituted with deuterium.

[0129] In the exemplary embodiment of the present disclosure, each of R41 to R48 may be selected from the group consisting of hydrogen, deuterium, a deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl group, and a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl group.

[0130] In an exemplary embodiment of the present disclosure, each of R41 to R48 may be selected from the group consisting of hydrogen, deuterium, a deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl group, and a deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroaryl group.

[0131] In an exemplary embodiment of the present disclosure, each of R41 to R48 may be selected from the group consisting of hydrogen, deuterium, a deuterated or undeuterated substituted or unsubstituted C6 to C20 aryl group, and a deuterated or undeuterated substituted or unsubstituted C2 to C20 heteroaryl group.

[0132] In an exemplary embodiment of the present disclosure, each of R41 to R48 may be selected from the group consisting of hydrogen, deuterium, a C6 to C20 aryl group which is unsubstituted or substituted with deuterium, and a C2 to C20 heteroaryl group which is unsubstituted or substituted with deuterium.

[0133] In an exemplary embodiment of the present disclosure, each of R41 to R48 may be selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted dibenzofuran, and unsubstituted or deuterium-substituted dibenzothiophene.

[0134] In exemplary embodiments of the present disclosure, the deuteration rate of the heterocyclic compound of Formula 1 may be 20% to 100%.

[0135] In exemplary embodiments of the present disclosure, the deuteration rate of the heterocyclic compound of Formula 1 may be 40% to 100%, preferably 50% to 100%.

[0136] In the exemplary embodiment of the present disclosure, the deuteration rate of the heterocyclic compound of Formula 1 satisfies the above range, and the photochemical properties of the compound without deuterium and the compound containing deuterium are almost similar. However, in the thin film, the material containing deuterium tends to be filled with a narrower intermolecular distance.

[0137] Therefore, when EOD (Electron Only Device) and HOD (Hole Only Device) were manufactured and the current density according to the voltage was examined, it can be seen that the deuterium-containing compound of Formula 1 according to the present application has a more balanced charge transport characteristic than the deuterium-free compound.

[0138] Furthermore, when the surface of the thin film was observed with an atomic force microscope (AFM), it could be seen that the thin film made of the deuterium-containing compound was deposited on a more uniform surface without aggregation.

[0139] In addition, the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, in the heterocyclic compound of Formula 1 having a deuteration rate within the above range according to the present disclosure, the stability of the entire molecule is increased, thereby improving the device life.

[0140] In exemplary embodiments of the present disclosure, the structure of Formula 1 may be divided into partial structures of Formulae 1-1 to 1-3.

[0141] [Formula 1-1]

[0142]

[0143] [Formula 1-2]

[0144]

[0145] [Formula 1-3]

[0146]

[0147] In Formulae 1-1 to 1-3, N-Het, R1 to R12, L, a and b are defined the same as in Formula 1, and the symbol It is the bonding position between the partial structures of Formula 1-1 to Formula 1-3.

[0148] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-1 in Formula 1 may have a deuteration rate of 0%.

[0149] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-1 in Formula 1 may have a deuteration rate of 100%.

[0150] In exemplary embodiments of the present disclosure, the partial structure of Formula 1-1 in Formula 1 may have a deuteration rate of 0% to 100%.

[0151] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-2 in Formula 1 may have a deuteration rate of 0%.

[0152] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-2 in Formula 1 may have a deuteration rate of 100%.

[0153] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-3 in Formula 1 may have a deuteration rate of 0%.

[0154] In an exemplary embodiment of the present disclosure, the partial structure of Formula 1-3 in Formula 1 may have a deuteration rate of 100%.

[0155] In an exemplary embodiment of the present disclosure, the partial structures of Formula 1-1 to Formula 1-3 in Formula 1 may have a deuteration rate of 100%.

[0156] In an exemplary embodiment of the present disclosure, the structure of Formula 1 can be divided into partial structures of Formulas 1-1 to 1-3, wherein the definitions of the substituents are the same as those in Formula 1, and the symbols is a bonding position between the partial structures of Formula 1-1 to Formula 1-3, and one of the partial structure of Formula 1-1, the partial structure of Formula 1-2, and the partial structure of Formula 1-3 in Formula 1 may have a deuteration rate of 100%.

[0157] For example, the structure of Formula 1 may be represented by Formula 1b, and each of a1, a2, and a3 may independently be 0 or a positive integer.

[0158] [Formula 1b]

[0159]

[0160] In Formula 1b, a1 may be a positive integer. Preferably, a1 may be a positive integer, and a2 and a3 may be 0. In this case, the life span and operating performance of the device may be improved while minimizing the increase in the production cost of the deuterated heterocyclic compound.

[0161] In Formula 1b, "D" represents a deuterium atom, and each of "a1", "a2" and "a3" represents the number of deuterium atoms. For example, "Da2" represents the number of deuterium atoms included in the dibenzofuran moiety.

[0162] In the exemplary embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be one of the compounds in Formula 1c, but is not limited thereto.

[0163] [Formula 1c]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[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]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259] In addition, by introducing various substituents into the structure of Formula 1, a compound having the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents of hole injection layer materials, hole transport materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials, which are mainly used to manufacture organic light-emitting devices, into the core structure, a compound that meets the conditions required for each organic material layer can be synthesized.

[0260] In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely controlled, the performance of the interface between organic materials can be improved, and the use of the material can be diversified.

[0261] In an exemplary embodiment of the present disclosure, the organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and at least one organic material layer located between the first electrode and the second electrode, and at least one of the at least one organic material layer includes at least one of the heterocyclic compounds in Formula 1.

[0262] In an exemplary embodiment of the present disclosure, the organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and at least one organic material layer between the first electrode and the second electrode, and at least one of the at least one organic material layer includes one of the heterocyclic compounds in Formula 1.

[0263] In an exemplary embodiment of the present disclosure, the organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and at least one organic material layer between the first electrode and the second electrode, and at least one of the at least one organic material layer includes two of the heterocyclic compounds in Formula 1.

[0264] When at least two of the heterocyclic compounds of the present disclosure are included in the organic light-emitting device, the heterocyclic compounds may be the same or different.

[0265] In an exemplary embodiment of the present disclosure, the first electrode may be an anode, and the second electrode may be a cathode.

[0266] In an exemplary embodiment of the present disclosure, the first electrode may be a cathode, and the second electrode may be an anode.

[0267] In an exemplary embodiment of the present disclosure, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound of Formula 1 may be included as a host material of a blue light-emitting layer in the blue organic light-emitting device.

[0268] In an exemplary embodiment of the present disclosure, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound of Formula 1 may be included as a host material of a green light-emitting layer in the green organic light-emitting device.

[0269] In an exemplary embodiment of the present disclosure, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound of Formula 1 may be included as a host material of a red light-emitting layer in a red organic light-emitting device.

[0270] The organic light-emitting device of the present disclosure may be manufactured by conventional methods and materials for manufacturing an organic light-emitting device, except for forming one or more organic material layers using the above-mentioned heterocyclic compound.

[0271] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed as an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method may be spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, and the like, but is not limited thereto.

[0272] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure. Alternatively, the organic material layer may have a multilayer structure including two or more layers. For example, the organic material layer may include a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (e.g., a light-emitting material layer (EML)), an electron transport layer (ETL), and an electron injection layer. However, the structure of the organic light-emitting device is not limited thereto, and the number of layers may be less than the above structure.

[0273] In the organic light-emitting device, the organic material layer includes an EML, and the EML may include the heterocyclic compound of Formula 1.

[0274] In the organic light-emitting device, the organic material layer includes an EML including a host material, and the host material may include the heterocyclic compound of Formula 1.

[0275] In an exemplary embodiment of the present disclosure, the EML may include the heterocyclic compound of Formula 1 as a host and an iridium compound as a dopant.

[0276] In the organic light-emitting device, the organic material layer may include an electron assisting layer including at least one of an EIL or an ETL, and the electron assisting layer may include the heterocyclic compound of Formula 1. That is, the EIL or the ETL may include the heterocyclic compound of Formula 1.

[0277] In the organic light-emitting device, the organic material layer may include an electron blocking layer (EBL) or a hole blocking layer (HBL), and the hole blocking layer (HBL) may include the heterocyclic compound of Formula 1.

[0278] The organic light-emitting device of the present disclosure may further include at least one selected from the group consisting of a HIL, a HTL, an ETL, an EIL, an EBL, and a HBL.

[0279] The stacking order of the electrodes and the organic material layers of the organic light-emitting device of the present disclosure is as follows: Figures 1 to 3 as shown in .

[0280] However, the scope of the present disclosure is not intended to be limited to these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present disclosure.

[0281] like Figure 1 As shown, an anode 200, an organic material layer (eg, an organic light emitting layer) 300, and a cathode 400 are sequentially stacked on a substrate 100 to form an organic light emitting device (eg, an organic light emitting diode). Figure 2 As shown, the cathode 400, the organic material layer 300, and the anode 200 may be sequentially stacked on the substrate 100 to form an organic light-emitting device.

[0282] Figure 3 An organic material layer having a multi-layer structure is shown. Figure 3 As shown, the organic material layer includes HIL 301, HTL 302, EBL 307, EML 303, HBL 304, ETL 305, and EIL 306. However, the structure of the organic material layer is not limited thereto. At least one organic material layer other than the EML may be omitted, or at least one functional layer may be further included.

[0283] The organic material layer including the compound of Formula 1 may further include another material.

[0284] Reference Figure 3 , the EML 303 may include the compound of Formula 1 as the first compound 312 .

[0285] In the organic light-emitting device according to the exemplary embodiment of the present disclosure, the organic material layer may further include the compound of Formula 2. For example, the EML 303 may include the compound of Formula 2 as the second compound 314, and the first compound 312 is the compound of Formula 1.

[0286] [Formula 2]

[0287]

[0288] In Formula 2, Ra and Rb are the same or different, and each of Ra and Rb is independently a deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl group.

[0289] Ra1 to Ra14 are the same or different, and each of Ra1 to Ra14 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more Ra1 to Ra14 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0290] Specifically, when the heterocyclic compound of Formula 2 is further included, an exciplex phenomenon may occur. The exciplex phenomenon refers to the formation of a binary complex in an excited state by electron exchange between a molecule having a strong donor property and a molecule having a strong acceptor property.

[0291] Figure 4 is a schematic diagram illustrating the phenomenon of exciplexes. Figure 4 As shown, when the exciplex phenomenon occurs, a new S1 level and a new T1 level are formed, and a red-shifted PL change can be confirmed from each molecule.

[0292] In this way, when the exciplex phenomenon occurs between the two molecules, reverse intersystem crossing (RISC) occurs, thereby increasing the internal quantum efficiency to 100%.

[0293] In particular, although the compound of formula 1 is a bipolar compound and does not have a strong acceptor ability. However, by injecting a donor (p-host), that is, a compound of formula 2 having good hole transport ability, a red-shifted PL change is shown. That is, the compound of formula 1 is included in the organic material layer together with the compound of formula 2, so that an exciplex phenomenon occurs and the luminescent properties are improved. In addition, since the heterocyclic compound (donor (p-host)) of formula 2 of the present disclosure having good hole transport ability is included, the life span can be significantly improved by the appropriate movement of the luminescent zone in the luminescent layer.

[0294] In an exemplary embodiment of the present disclosure, Ra and Rb in Formula 2 may be the same or different, and each of Ra and Rb may be a deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl group; or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl group.

[0295] In an exemplary embodiment of the present disclosure, Ra and Rb in Formula 2 may be the same or different, and each of Ra and Rb may be a deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl group; or a deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroaryl group.

[0296] In an exemplary embodiment of the present disclosure, Ra and Rb in Formula 2 may be the same or different, and each of Ra and Rb may be a C6 to C30 aryl group which is unsubstituted or substituted with deuterium, a C1 to C30 alkyl group, or a C6 to C30 aryl group; or a C2 to C30 heteroaryl group which is unsubstituted or substituted with deuterium.

[0297] In an exemplary embodiment of the present disclosure, Ra and Rb in Formula 2 may be the same or different, and each of Ra and Rb may be selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.

[0298] In an exemplary embodiment of the present disclosure, Ra1 and Ra14 in Formula 2 may be the same or different, and each of Ra1 and Ra14 may be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more Ra1 and Ra14 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0299] In an exemplary embodiment of the present disclosure, Ra1 and Ra14 may be the same or different, and each of Ra1 and Ra14 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more Ra1 and Ra14 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

[0300] In an exemplary embodiment of the present disclosure, Ra1 and Ra14 may be the same or different, and each of Ra1 and Ra14 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C40 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C40 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C40 heteroaryl, or two or more Ra1 and Ra14 may be bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C40 heterocyclic ring.

[0301] In an exemplary embodiment of the present disclosure, Ra1 and Ra14 may be the same or different, and each of Ra1 and Ra14 may be independently selected from the group consisting of: hydrogen; deuterium; deuterated or undeuterated substituted or unsubstituted C1 to C20 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C20 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C20 heteroaryl.

[0302] In an exemplary embodiment of the present disclosure, Ra1 and Ra14 may be the same or different, and each of Ra1 and Ra14 may be hydrogen or deuterium.

[0303] In exemplary embodiments of the present disclosure, the deuteration rate of the heterocyclic compound of Formula 2 may be 20% to 100%.

[0304] In exemplary embodiments of the present disclosure, the deuteration rate of the heterocyclic compound of Formula 2 may be 25% to 100%, preferably 30% to 100%.

[0305] In an exemplary embodiment of the present disclosure, the structure of Formula 2 may be divided into partial structures in Formula 2-1 to Formula 2-3.

[0306] [Formula 2-1]

[0307]

[0308] [Formula 2-2]

[0309]

[0310] [Formula 2-3]

[0311]

[0312] In Formula 2-1 to Formula 2-3, the definitions of substituents are the same as those in Formula 2, and the symbols It is the bonding position between the partial structures of Formula 2-1 to Formula 2-3.

[0313] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-1 in Formula 2 may have a deuteration rate of 0%.

[0314] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-1 in Formula 2 may have a deuteration rate of 100%.

[0315] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-1 in Formula 2 may have a deuteration rate of 0% to 100%.

[0316] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-2 in Formula 2 may have a deuteration rate of 0%.

[0317] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-2 in Formula 2 may have a deuteration rate of 100%.

[0318] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-3 in Formula 2 may have a deuteration rate of 0%.

[0319] In an exemplary embodiment of the present disclosure, the partial structure of Formula 2-3 in Formula 2 may have a deuteration rate of 100%.

[0320] In an exemplary embodiment of the present disclosure, the partial structures of Formula 2-1 to Formula 2-3 in Formula 2 may have a deuteration rate of 100%.

[0321] When the compound of Formula 1 and the compound of Formula 2 are simultaneously included in the organic material layer of the organic light-emitting device, better efficiency and lifespan effects are exhibited. When both compounds are simultaneously included, an exciplex phenomenon can be expected.

[0322] In the exciplex phenomenon, the energy with the HOMO level of the donor (p-main body) and the LUMO level intensity of the acceptor (n-main body) is emitted by the electron exchange between the two molecules. When the exciplex phenomenon occurs between the two molecules, a reverse intersystem crossing (RISC) occurs, thereby increasing the internal quantum efficiency of fluorescence to 100%. When a donor donor (p-main body) with good hole transport ability and an acceptor (n-main body) with good electron transport ability are used as the main body of the light-emitting layer, since holes are injected into the p-main body and electrons are injected into the n-main body, the driving voltage can be reduced and the life span can be increased.

[0323] In exemplary embodiments of the present disclosure, the heterocyclic compound of Formula 2 may be one of the compounds in Formula 2a.

[0324] [Formula 2a]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336] In the organic light-emitting device of the present disclosure, the organic material layer may include a deuterium-containing heterocyclic compound of Formula 1 (e.g., a "deuterated heterocyclic compound"), a deuterated heterocyclic compound of Formula 1 and a heterocyclic compound with a deuteration rate of 0% of Formula 2 (e.g., a "non-deuterated heterocyclic compound"), or a deuterated heterocyclic compound of Formula 1 and a deuterated heterocyclic compound of Formula 2.

[0337] In the organic light-emitting device of the present disclosure including an N-type compound (ie, a compound of Formula 1) and a P-type compound (ie, a compound of Formula 2), device performance may be further improved as more deuterium is substituted on the compound of Formula 1 (ie, the N-type compound). That is, the compound of Formula 1 may have a first deuteration rate, and the compound of Formula 2 may have a second deuteration rate that is less than the first deuteration rate.

[0338] In the organic light-emitting device of the present disclosure, the compound of Formula 2 may be included in the EML of the organic material layer.

[0339] In the organic light-emitting device of the present disclosure, the compound of Formula 2 may be included in the EML of the organic material layer as a host material.

[0340] In the organic light-emitting device of the present disclosure, the host material in the EML of the organic material layer may include both the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2.

[0341] In an exemplary embodiment of the present disclosure, a composition for an organic material layer of an organic light-emitting device including a heterocyclic compound of Formula 1 and a heterocyclic compound of Formula 2 is provided.

[0342] In the composition, the weight ratio of the heterocyclic compound of Formula 1 to the heterocyclic compound of Formula 2 may be 1:10 to 10:1, advantageously 1:8 to 8:1, more advantageously 1:5 to 5:1, further advantageously 1:2 to 2:1, but not limited thereto. For example, the weight ratio of the compound of Formula 2 may be greater than the weight ratio of the compound of Formula 1. In this case, the hole injection and transport characteristics in the device are improved, thereby reducing the driving voltage of the device.

[0343] The composition can be used to form an organic material of an organic light-emitting device. Preferably, the composition can be used to form a host of an EML.

[0344] The composition is in the form of a simple mixture of two or more compounds. The materials in a powder state may be mixed before forming the organic material layer of the organic light-emitting device, or the compounds in a liquid state may be mixed at an appropriate temperature or higher. The composition is solid below the melting point of each material and can be kept in a liquid state by adjusting the temperature.

[0345] The composition may further include materials known in the art, such as solvents and additives.

[0346] The organic light-emitting device according to the exemplary embodiment of the present disclosure may be manufactured according to a conventional organic light-emitting device manufacturing method and materials except that the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are used to form one or more organic material layers.

[0347] In an exemplary embodiment of the present disclosure, a method for manufacturing an organic light-emitting device includes: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer. The step of forming one or more organic material layers includes using a composition for an organic material layer of the present disclosure.

[0348] In an exemplary embodiment of the present disclosure, the step of forming the organic material layer includes premixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2, and forming the organic material layer using the mixture by thermal vacuum deposition.

[0349] In this case, the pre-mixing step may mean mixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 and storing the mixture in a bottle before depositing the mixture.

[0350] In the present disclosure, the premix may be referred to as a composition for an organic material layer.

[0351] The anode may include a material having a relatively high work function, such as a transparent conductive oxide, a metal, or a conductive polymer. For example, the anode may be formed of a metal such as vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb; a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole or polyaniline, but not limited thereto.

[0352] The cathode may include a material having a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. For example, the cathode may be formed of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or alloys thereof; or a multilayer structure such as LiF / Al or LiO 2 / Al, but not limited to this.

[0353] As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound disclosed in U.S. Patent No. 4,356,429, such as copper phthalocyanine; a starburst-type amine derivative disclosed in Advanced Material, 6, p. 677 (1994), such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), or 1,3,5-tri[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB); or a conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate); and the like.

[0354] For example, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, or triphenyldiamine derivatives may be used as the hole transport material. The hole transport material may be a low molecular weight or high molecular weight polymer material.

[0355] For example, 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, diphenyl dicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes (such as 8-hydroxyquinoline) and its derivatives can be used as electron transport materials. The electron transport material can be a low molecular weight or high molecular polymer material.

[0356] As the electron injection material, LiF is generally used, but is not limited thereto.

[0357] As the luminescent material, a red, green or blue luminescent material can be used, and if necessary, two or more luminescent materials can be mixed and used. In this case, the two or more luminescent materials can be deposited from separate sources, or can be premixed and deposited from a single source. In addition, the luminescent material can be a fluorescent material or a phosphorescent material. As the luminescent material, a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, can be used alone, but a material that participates in luminescence together with a host material and a dopant material can be used.

[0358] When the host materials of the light-emitting materials are mixed and used, the same type of host materials may be mixed and used, or different types of host materials may be mixed and used. For example, two or more types of n-type host materials or p-type host materials may be selected and used as host materials for the light-emitting layer.

[0359] The organic light-emitting device according to the exemplary embodiment of the present disclosure may be a top emission type, a bottom emission type, or a dual-side emission type according to the materials used.

[0360] The heterocyclic compound according to the exemplary embodiment of the present disclosure may function in a principle similar to that of an organic light-emitting device applied to organic electronic devices including an organic solar cell, an organic photoreceptor, and an organic transistor.

[0361] Hereinafter, the present specification will be described in more detail through examples, but these examples are only used to illustrate the present disclosure and are not used to limit the scope of the present disclosure.

[0362] [synthesis]

[0363] [Synthesis 1] Compound 3 (E)

[0364]

[0365] (1) Compound [A]-1

[0366] In a single-necked round-bottom flask, a mixture of 3-phenyl-9H-carbazole (10 g, 0.041 mol), trifluoromethanesulfonic acid (34 g, 0.23 mol) and D6-benzene (200 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound [A]-1. (7.02 g, 67%)

[0367] (2) Compound 3-1

[0368] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (12.64 g, 0.050 mol), Cs 2 CO 3 (29.32 g, 0.09 mol), and dimethylacetamide (100 mL) were refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent, and purified by column to obtain compound 3-1. (17.03 g, 83%)

[0369] (3) Compound 3-2

[0370] In a single-necked round-bottom flask, 9-(7-chlorobenzo[b,d]furan-4-yl)-3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (17.03 g, 0.037 mol), bis(pinacolato)diboron (18.79 g, 0.074 mol), Pd(dba) 2 A mixture of (3.39 g, 0.0037 mol), Xphos (3.53 g, 0.0074 mol), potassium acetate (10.89 g, 0.11 mol) and 1,4-dioxane (170 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 3-2 (19.85 g, 98%).

[0371] (4) Compound 3[E]

[0372] In a single-necked round-bottom flask, 3-(phenyl-d5)-9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (19.85 g, 0.036 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.71 g, 0.040 mol), Pd(PPh 3 ) 4 (2.08g, 0.0018mol), K 2 CO 3 A mixture of (9.95 g, 0.072 mol), 1,4-dioxane (170 mL) and water (80 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 3[E]. (17.16 g, 73%)

[0373] The following Compound E was synthesized in the same manner as in Synthesis 1, except that Intermediates A, B and C of Table 1 were used.

[0374] Table 1

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387] [Synthesis 2] Compound 71(F)

[0388]

[0389] (1) Compound [A]-1

[0390] In a single-necked round-bottom flask, a mixture of 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), trifluoromethanesulfonic acid (34 g, 0.23 mol) and D6-benzene (200 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound [A]-1. (9.89 g, 97%)

[0391] (2) Compound 71-1

[0392] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan-1,2,4,7,8,9-d6 (9.89 g, 0.044 mol), 3-phenyl-9H-carbazole (11.78 g, 0.048 mol), Cs 2 CO 3 A mixture of (28.67 g, 0.088 mol) and dimethylacetamide (100 mL) was refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent, and purified by column to obtain compound 71-1. (16.83 g, 85%)

[0393] (3) Compound 71-2

[0394] In a single-necked round-bottom flask, 9-(7-chlorodibenzo[b,d]furan-4-yl-1,2,3,6,8,9-d6)-3-phenyl-9H-carbazole (16.83 g, 0.037 mol), bis(pinacol)diboron (18.79 g, 0.074 mol), Pd(dba) 2 A mixture of (3.39 g, 0.0037 mol), Xphos (3.53 g, 0.0074 mol), potassium acetate (10.89 g, 0.11 mol) and 1,4-dioxane (160 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 71-2. (19.43 g, 97%)

[0395] (4) Compound 71[E]

[0396] In a single-necked round-bottom flask, 3-phenyl-9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl-1,2,3,6,8,9-d6)-9H-carbazole (19.43 g, 0.036 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.71 g, 0.040 mol), Pd(PPh 3 ) 4 (2.08g, 0.0018mol), K 2 CO 3 A mixture of (9.95 g, 0.072 mol), 1,4-dioxane (190 mL) and water (80 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain Compound 71[F]. (16.30 g, 70%)

[0397] The following Compound F was synthesized in the same manner as in Synthesis 2, except that Intermediates A, B and C of Table 2 were used.

[0398] Table 2

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405] [Synthesis 3] Compound 137 (G)

[0406]

[0407] (1) Compound [A]-1

[0408] In a single-necked round-bottom flask, 2,4,6-trichloro-1,3,5-triazine (10 g, 0.054 mol), 1-bromobenzene-2,3,4,5,6-d5 (9.63 g, 0.059 mol), Pd(PPh 3 ) 4 (3.12g, 0.0027mol), K 2 CO 3 A mixture of (14.93 g, 0.11 mol), tetrahydrofuran (100 mL) and water (30 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound [A]-1. (6.99 g, 56%)

[0409] (2) Compound [A]-2

[0410] In a single-necked round-bottom flask, 2,4-dichloro-6-(phenyl-d5)-1,3,5-triazine (6.99 g, 0.030 mol), 1-bromobenzene-2,3,4,5,6-d5 (5.35 g, 0.033 mol), Pd(PPh 3 ) 4 (1.73 g, 0.0015 mol), K 2 CO 3 A mixture of (8.29 g, 0.06 mol), tetrahydrofuran (70 mL) and water (20 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound [A]-2. (5.58 g, 67%)

[0411] (3) Compound 137-1

[0412] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), 9H-carbazole (8.28 g, 0.050 mol), Cs 2 CO 3 A mixture of (29.32 g, 0.09 mol) and dimethylacetamide (100 mL) was refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent and purified by column to obtain compound 137-1. (15.39 g, 93%)

[0413] (4) Compound 137-2

[0414] In a single-necked round-bottom flask, a mixture of 9-(7-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (15.39 g, 0.042 mol), bis(pinacolato)diboron (21.33 g, 0.084 mol), Pd(dba)2 (3.85 g, 0.0042 mol), Xphos (4.00 g, 0.0084 mol), potassium acetate (12.37 g, 0.13 mol) and 1,4-dioxane (150 mL) was refluxed at 120°C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 137-2. (18.33 g, 95%)

[0415] (5) Compound 137[G]

[0416] In a single-necked round-bottom flask, 9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole (18.33 g, 0.040 mol), 2-chloro-4,6-bis(phenyl-5d)-1,3,5-triazine (12.22 g, 0.044 mol), Pd(PPh 3 ) 4 (2.31 g, 0.002 mol), K 2 CO 3 A mixture of (11.06 g, 0.008 mol), 1,4-dioxane (180 mL) and water (50 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 137[G]. (16.78 g, 73%)

[0417] When compound A and A' are the same, A-2 can be directly synthesized by adding 2 equivalents of compound A in the first reaction. That is, when A and A' are the same, the second reaction step can be omitted.

[0418] The following Compound G was synthesized in the same manner as in Synthesis 3, except that Intermediates A, A′, B, and C of Table 3 were used.

[0419] Table 3

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430] [Synthesis 4] Compound 641 (H)

[0431]

[0432] (1) Compound [A]-1

[0433] In a single-necked round-bottom flask, 2,4,6-trichloro-1,3,5-triazine (10 g, 0.054 mol), 1-bromobenzene-2,3,4,5,6-d5 (9.63 g, 0.059 mol), Pd(PPh 3 ) 4 (3.12g, 0.0027mol), K 2 CO 3 A mixture of (14.93 g, 0.11 mol), tetrahydrofuran (100 mL) and water (30 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound [A]-1. (6.99 g, 56%)

[0434] (2) Compound [A]-2

[0435] In a single-necked round-bottom flask, 2,4-dichloro-6-(phenyl-d5)-1,3,5-triazine (6.99 g, 0.030 mol), 1-bromobenzene-2,3,4,5,6-d5 (5.35 g, 0.033 mol), Pd(PPh 3 ) 4 (1.73 g, 0.0015 mol), K 2 CO 3 A mixture of (8.29 g, 0.06 mol), tetrahydrofuran (70 mL) and water (20 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound [A]-2. (5.58 g, 67%)

[0436] (3) Compound 641-1

[0437] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), 9H-carbazole (8.28 g, 0.050 mol), Cs2 CO 3 A mixture of (29.32 g, 0.09 mol) and dimethylacetamide (100 mL) was refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent and purified by column to obtain compound 641-1. (15.39 g, 93%)

[0438] (4) Compound 641-2

[0439] In a single-necked round-bottom flask, a mixture of 9-(7-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (15.39 g, 0.042 mol), trifluoromethanesulfonic acid (51 g, 0.34 mol) and D6-benzene (150 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound 641-2. (10.11 g, 63%)

[0440] (5) Compound 641-3

[0441] In a single-necked round-bottom flask, 9-(7-chlorodibenzo[b,d]furan-4-yl-1,2,3,6,8,9-d6)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (10.11 g, 0.026 mol), bis(pinacolato)diboron (13.20 g, 0.052 mol), Pd(dba) 2 A mixture of (2.38 g, 0.0026 mol), Xphos (2.48 g, 0.0052 mol), potassium acetate (7.66 g, 0.078 mol) and 1,4-dioxane (100 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 641-3. (11.30 g, 92%)

[0442] (6) Compound 641[H]

[0443] In a single-necked round-bottom flask, a mixture of (2-(6-(9H-carbazol-9-yl-d8)dibenzo[b,d]furan-3-yl-1,2,4,7,8,9-d6)-4,5,5-trimethyl-1,3,2-dioxaborolan-4-yl)methyl (11.30 g, 0.024 mol), 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (7.33 g, 0.026 mol), Pd(PPh3)4 (1.39 g, 0.0012 mol), K2CO3 (6.63 g, 0.048 mol), 1,4-dioxane (110 mL) and water (50 mL) was refluxed at 120°C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 641[H]. (11.73 g, 83%)

[0444] When compound A and A' are the same, compound A-2 can be directly synthesized by adding 2 equivalents of compound A in the first reaction. That is, when compound A and A' are the same, the second reaction step can be omitted.

[0445] The following Compound H was synthesized in the same manner as in Synthesis 4, except that Intermediates A, A′, B, and C of Table 4 were used.

[0446] Table 4

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456] [Synthesis 5] Compound 797(I)

[0457]

[0458] (1) Compound 797-1

[0459] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), 3-phenyl-9H-carbazole (12.17 g, 0.050 mol), Cs 2 CO 3 A mixture of (29.32 g, 0.09 mol) and dimethylacetamide (100 mL) was refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent and purified by column to obtain compound 797-1. (18.18 g, 91%)

[0460] (2) Compound 797-2

[0461] In a single-necked round-bottom flask, a mixture of 9-(7-chlorodibenzo[b,d]furan-4-yl)-3-phenyl-9H-carbazole (18.18 g, 0.041 mol), trifluoromethanesulfonic acid (49.23 g, 0.33 mol) and D6-benzene (182 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound 797-2. (12.94 g, 68%)

[0462] (3) Compound 797-3

[0463] In a single-necked round-bottom flask, 9-(7-chlorodibenzo[b,d]furan-4-yl-1,2,3,6,8,9-d6)-3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (12.94 g, 0.028 mol), bis(pinacolato)diboron (14.22 g, 0.056 mol), Pd(dba) 2 A mixture of (2.56 g, 0.0028 mol), Xphos (2.67 g, 0.0056 mol), potassium acetate (8.24 g, 0.084 mol) and 1,4-dioxane (130 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 797-3. (13.48 g, 87%)

[0464] (4) Compound 797[I]

[0465] In a single-necked round-bottom flask, a mixture of 3-(phenyl-d5)-9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl-1,2,3,6,8,9-d6)-9H-carbazole-1,2,4,5,6,7,8-d7 (13.48 g, 0.024 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.96 g, 0.026 mol), Pd(PPh3)4 (1.39 g, 0.0012 mol), K2CO3 (6.63 g, 0.048 mol), 1,4-dioxane (130 mL) and water (40 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 797[I]. (12.33g, 78%)

[0466] The following Compound I was synthesized in the same manner as in Synthesis 5, except that Intermediates A, B and C of Table 5 were used.

[0467] Table 5

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475] [Synthesis 6] Compound 929 (J)

[0476]

[0477] (1) Compound 929-1

[0478] In a single-necked round-bottom flask, 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), bis(pinacol)diboron (22.85 g, 0.090 mol), Pd(dba) 2A mixture of 2-(4.12)g, 0.0045mol), Xphos (8.58g, 0.018mol), potassium acetate (13.25g, 00.14mol) and 1,4-dioxane (100mL) was refluxed at 120°C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 929-1. (13.77g, 98%)

[0479] (2) Compound 929-2

[0480] In a single-necked round-bottom flask, 2-(6-fluorodibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.77 g, 0.044 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.96 g, 0.048 mol), Pd(PPh 3 ) 4 (2.54 g, 0.0022 mol), K 2 CO 3 A mixture of (12.16 g, 0.088 mol), 1,4-dioxane (130 mL) and water (40 mL) was refluxed at 120° C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 929-2. (12.49 g, 68%)

[0481] (3) Compound 929-3

[0482] In a single-necked round-bottom flask, a mixture of 2-(6-fluorodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine (12.49 g, 0.030 mol), trifluoromethanesulfonic acid (36.02 g, 0.24 mol) and D6-benzene (130 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound 929-3. (10.01 g, 77%)

[0483] (4) Compound 929-J

[0484] In a single-necked round-bottom flask, 2-(6-fluorodibenzo[b,d]furan-3-yl-1,2,4,7,8,9-d6)-4,6-bis(phenyl-d5)-1,3,5-triazine (10.01 g, 0.023 mol), 2-phenyl-9H-carbazole (6.16 g, 0.025 mol), Cs 2 CO 3A mixture of (14.99 g, 0.046 mol) and dimethylacetamide (100 mL) was refluxed at 170° C. After cooling, the resultant was filtered to remove the solvent and purified by column to obtain compound 929[J]. (14.05 g, 93%)

[0485] The following Compound J was synthesized in the same manner as in Synthesis 6, except that Intermediates A, B and C of Table 6 were used.

[0486] Table 6

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493] [Synthesis 7] Compound 1073 (K)

[0494]

[0495] (1) Compound 1073-1

[0496] In a single-necked round-bottom flask, a mixture of 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 0.045 mol), bis(pinacolato)diboron (22.85 g, 0.090 mol), Pd(dba)2 (4.12 g, 0.0045 mol), Xphos (8.58 g, 0.018 mol), potassium acetate (13.25 g, 00.14 mol) and 1,4-dioxane (100 mL) was refluxed at 120°C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 1073-1. (13.77 g, 98%)

[0497] (2) Compound 1073-2

[0498] In a single-necked round-bottom flask, a mixture of 2-(6-fluorodibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.77 g, 0.044 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.96 g, 0.048 mol), Pd(PPh3)4 (2.54 g, 0.0022 mol), K2CO3 (12.16 g, 0.088 mol), 1,4-dioxane (130 mL) and water (40 mL) was refluxed at 120°C. After cooling, the resultant was concentrated and filtered through silica gel to obtain compound 1073-2. (12.49 g, 68%)

[0499] (3) Compound 1073[K]

[0500] In a single-necked round-bottom flask, a mixture of 2-(6-fluorodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine (12.49 g, 0.030 mol), 2-phenyl-9H-carbazole (8.03 g, 0.00.033 mol), Cs2CO3 (19.55 g, 0.060 mol) and dimethylacetamide (120 mL) was refluxed at 170°C. After cooling, the resultant was filtered to remove the solvent and purified by column to obtain compound 1073[K]. (16.92 g, 88%)

[0501] The following compound K was synthesized in the same manner as in Synthesis 7, except that the intermediates A, B and C of Table 7 were used.

[0502] Table 7

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509] [Synthesis 8] Compound 2-2 (E)

[0510]

[0511] (1) Compound 2-2-1

[0512] In a single-necked round-bottom flask, 9H, 9'H-3,3'-bicarbazole (10 g, 0.030 mol), 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (7.26 g, 0.030 mol), CuI (0.57 g, 0.003 mol), trans-1,4-diaminocyclohexane (0.34 g, 0.003 mol) and K3PO4 (12.74 g, 0.06 mol) were dissolved in 100 mL of 1,4-oxane at 125 ° C, and the mixture was refluxed for 8 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction. The organic layer was dried with MgSO4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized with methanol to obtain compound 2-2-1. (13.92g, 94%)

[0513] (2) Compound 2-2[E]

[0514] In a single-necked round-bottom flask, 9-([1,1'-biphenyl]-4-yl-d9)-9H,9'H-3,3'-bicarbazole (13.92 g, 0.028 mol), 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (6.83 g, 0.028 mol), CuI (0.53 g, 0.0028 mol), trans-1,4-diaminocyclohexane (0.32 g, 0.0028 mol), K 3 PO 4 (11.89 g, 0.056 mol) was dissolved in 140 mL of 1,4-oxane at 125 ° C, and the mixture was refluxed for 8 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction. The organic layer was dried with MgSO4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain compound 2-2 [E]. (16.14 g, 88%)

[0515] When compound A and A' are the same, compound 2-2[E] can be directly synthesized by adding 2 equivalents of compound A in the first reaction. That is, when compound A and A' are the same, the second reaction step can be omitted.

[0516] The following compound B was synthesized in the same manner as in Synthesis 8, except that the intermediates A and A' in Table 8 were used.

[0517] Table 8

[0518]

[0519]

[0520]

[0521] [Synthesis 9] Compound 2-26 (E)

[0522]

[0523] (1) Compound 2-26-1

[0524] In a single-necked round-bottom flask, a mixture of 9H,9'H-3,3'-bicarbazole (10 g, 0.030 mol), trifluoromethanesulfonic acid (34 g, 0.023 mol) and D6-benzene (100 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound 2-26-1. (7.07 g, 68%)

[0525] (2) Compound 2-26-2

[0526] In a single-necked round-bottom flask, 9H, 9'H-3,3'-bicarbazole-1,1',2,2',4,4',5,5',6,6',7,7',8,8'-d14 (7.07 g, 0.02 mol), CuI (0.38 g, 0.002 mol), trans-1,4-diaminocyclohexane (0.23 g, 0.002 mol), K3PO4 (8.49 g, 0.04 mol) were dissolved in 70 mL of 1,4-oxane at 125 ° C, and the mixture was refluxed for 8 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction. The organic layer was dried with MgSO4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain compound 2-26-2. (8.28 g, 83%)

[0527] (3) Compound 2-26[E]

[0528] In a single-necked round-bottom flask, 9-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole-1,1',2,2',4,4',5,5',6,6',7,7',8,8'-d14 (8.28 g, 0.017 mol), CuI (0.32 g, 0.0017 mol), trans-1,4-diaminocyclohexane (0.19 g, 0.0017 mol), and K3PO4 (7.22 g, 0.034 mol) were dissolved in 80 mL of 1,4-oxane and refluxed at 125 °C for 8 hours. After the reaction was completed, distilled water and DCM were added for extraction at room temperature, and the organic layer was washed with MgSO 4 The solvent was dried and removed by rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain compound 2-26 [E]. (8.63 g, 78%)

[0529] When compound A and A' are the same, compound 2-26[E] can be directly synthesized by adding 2 equivalents of compound A in the first reaction. That is, when compound A and A' are the same, the second reaction step can be omitted.

[0530] The following compound C was synthesized in the same manner as in Synthesis 9, except that the intermediates A and A' in Table 9 were used.

[0531] Table 9

[0532]

[0533] [Synthesis 10] Compound 2-50 (E)

[0534]

[0535] (1) Compound 2-50-1

[0536] In a single-necked round-bottom flask, 9-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole (10 g, 0.021 mol), CuI (0.40 g, 0.0021 mol), trans-1,4-diaminocyclohexane (0.024 g, 0.0021 mol), and K3PO4 (8.92 g, 0.042 mol) were dissolved in 100 mL of 1,4-oxane and refluxed at 125 °C for 8 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was washed with MgSO 4 The solvent was dried and removed by rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized with methanol to obtain compound 2-50-1. (12.17 g, 91%)

[0537] (2) Compound 2-50-E

[0538] In a single-necked round-bottom flask, a mixture of 9,9'-di([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole (12.17 g, 0.017 mol), trifluoromethanesulfonic acid (40.8 g, 0.27 mol) and D6-benzene (120 mL) was refluxed at 70 °C. 2 After quenching and extraction with O, the resultant was concentrated and filtered through silica gel. After concentration, the resultant was treated with methanol to obtain compound 2-50[E]. (8.87 g, 78%)

[0539] The following compound D was synthesized in the same manner as in Synthesis 10, except that the intermediates A and B of Table 10 were used.

[0540] Table 10

[0541]

[0542]

[0543] In the reaction of replacing hydrogen with deuterium in an organic compound, as the reaction temperature increases, the substitution rate of hydrogen for deuterium increases and the yield decreases.

[0544] In addition to the compounds described in Synthesis 1 to 10 and Tables 1 to 10, compounds represented by Formula 1 and Formula 2 were also synthesized in the same manner as described in Synthesis.

[0545] The data of the synthesized compounds are shown in Tables 11 and 12.

[0546] [Table 11]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554] [Table 12]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566] [Example]

[0567] [Example 1_Organic Light Emitting Device]

[0568] The coating was cleaned with distilled water and ultrasonic A glass substrate with an ITO film is formed. After cleaning with distilled water, the glass substrate is cleaned by ultrasonic cleaning with a solvent such as acetone, methanol, isopropanol, etc., and dried. The glass substrate is UVO treated for 5 minutes using UV in a UV cleaner. After the glass substrate is transferred to a plasma cleaner (PT), plasma treatment is performed in a vacuum state to remove the ITO work function and residual film, and then transferred to a thermal deposition device for organic deposition.

[0569] A hole injection layer of 2-TNATA (4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine) was formed as a common layer on an ITO transparent electrode (anode), and a hole transport layer of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed on the hole injection layer.

[0570] The light emitting layer was deposited on the hole transport layer by thermal vacuum deposition as follows. By using a compound as a host, Ir(ppy) 3 As a green dopant, the doping rate is 7% and the deposition thickness is The light-emitting layer is formed by depositing BCP on the light-emitting layer. The hole blocking layer is formed by depositing Alq 3 Formed on the hole blocking layer The electron transport layer is formed by depositing lithium fluoride (LiF) on the electron transport layer. The electron injection layer is formed by depositing Al on the electron injection layer. of the cathode, thereby manufacturing an organic light-emitting device.

[0571] All organic compounds required for the organic light-emitting device were added in 10 -6 Up to 10 -8 Vacuum sublimation and purification were carried out under conditions of 2000 torr.

[0572] [Driving Voltage and Luminous Efficiency of Organic Light-Emitting Device]

[0573] The electroluminescence (EL) characteristics of the organic light-emitting device were measured using McScience’s M7000, and the lifetime measurement device (M6000) was used at a reference brightness of 6,000 cd / m 2 Measure T 90 The electroluminescence (EL) characteristics of the organic light-emitting device are listed in Table 13.

[0574] Table 13

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583] [Example 2_Organic Light Emitting Device]

[0584] The coating was cleaned with distilled water and ultrasonic A glass substrate with an ITO film is formed. After cleaning with distilled water, the glass substrate is cleaned by ultrasonic cleaning with a solvent such as acetone, methanol, isopropanol, etc., and dried. The glass substrate is UVO treated for 5 minutes using UV in a UV cleaner. After the glass substrate is transferred to a plasma cleaner (PT), plasma treatment is performed in a vacuum state to remove the ITO work function and residual film, and then transferred to a thermal deposition device for organic deposition.

[0585] A hole injection layer of 2-TNATA (4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine) was formed as a common layer on an ITO transparent electrode (anode), and a hole transport layer of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed on the hole injection layer.

[0586] The light emitting layer was deposited on the hole transport layer by thermal vacuum deposition as follows. By using a compound as a host, Ir(ppy) 3 As a green dopant, the doping rate is 7% and the deposition thickness is The light-emitting layer is formed by depositing BCP on the light-emitting layer. The hole blocking layer is formed by depositing Alq 3 Formed on the hole blocking layer The electron transport layer is formed by depositing lithium fluoride (LiF) on the electron transport layer. The electron injection layer is formed by depositing Al on the electron injection layer. of the cathode, thereby manufacturing an organic light-emitting device.

[0587] All organic compounds required for the organic light-emitting device were added in 10 -6 Up to 10 -8 Vacuum sublimation and purification were carried out under conditions of 2000 torr.

[0588] The electroluminescence (EL) characteristics of the organic light-emitting device were measured using McScience’s M7000, and the lifetime measurement device (M6000) was used at a reference brightness of 6,000 cd / m 2 Measure T 90 . Driving voltage (V), luminous efficiency (cd / A), CIE and lifetime (T 90 ) are listed in Table 14.

[0589] Table 14

[0590]

[0591]

[0592]

[0593]

[0594]

[0595] As a result of the above-mentioned device evaluation, as the deuteration rate of the heterocyclic compound is higher, the driving voltage is lower and the life is longer. When the dibenzofuran part (a part) used as a linker for connecting the electron transport part and the hole transport part is replaced by deuterium (D), the driving voltage is improved compared with the non-deuterated compound. However, the effect of the deuterium-substituted compound on the dibenzofuran part is less than that of the deuterium-substituted compound on the electron transport part and the hole transport part. The vibration frequency of the intramolecular bond of the triazine and carbazole parts that directly exchange electrons is constantly changing due to the movement of electrons, thereby affecting the stability and molecular structure of the intramolecular bond.

[0596] By substituting with deuterium, which has a higher molecular weight than hydrogen, the change in vibration frequency is reduced, thereby lowering the energy of the molecule. As a result, the stability of the molecule is increased.

[0597] Specifically, in the device evaluation, when the deuteration rate of the compound of Formula 2 of the present disclosure is higher than the deuteration rate of the compound of Formula 1 of the present disclosure, the performance of the device is further improved.

[0598] The EBL 307 may include the compound of Formula 10 as the electron blocking material 322 .

[0599] [Formula 10]

[0600]

[0601] In Formula 10, each of R51 and R52 is independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group, or two R51 and R52 are connected to form a ring. In addition, b1 is an integer from 0 to 4, and b2 is an integer from 0 to 5. Each of R53 and R54 is independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group, or two R53 and R54 are connected to form a ring. In addition, b3 is an integer from 0 to 4, and b4 is an integer from 0 to 5. Each of R55 and R56 is hydrogen, or two R55 and R56 are connected to form a ring. In addition, each of c1, c2 and c3 is independently 0 or a positive integer, and at least one of c1, c2 and c3 is a positive integer. In Formula 10, D represents a deuterium atom, and each of c1, c2 and c3 represents the number of deuterium atoms.

[0602] That is, in the compound of Formula 10, at least one hydrogen is substituted with a deuterium atom.

[0603] For example, c1 can be a positive integer. Preferably, c1 is a positive integer, and c2 and c3 are 0. In Formula 10, when only the fluorene part or the spirofluorene part is deuterated, the life and driving performance of the device can be improved while minimizing the increase in production cost due to deuterium atoms. In this case, the deuteration rate of the fluorene part or the spirofluorene part can be 100%.

[0604] The compound of Formula 10 may be one of the compounds of Formula 11.

[0605] [Formula 11]

[0606]

[0607]

[0608]

[0609]

[0610]

[0611] When the EML 303 includes the first compound 312 as an N-type host (which is the compound in Formula 1), the second compound 314 as a P-type host (which is the compound in Formula 2), and the third compound 316 as a dopant (which is an iridium complex, such as Ir(ppy) 3 ), and when the EBL 307 adjacent to the EML 303 includes the electron blocking material 322 as the compound of Formula 10, the light emitting characteristics of the organic light emitting device are significantly improved. For example, the third compound 316 as a dopant may be Ir(ppy) 3 .

[0612] In addition, when c1 in Formula 10 is a positive integer and c2 and c3 in Formula 10 are 0, the light emitting characteristics of the organic light emitting device are further improved.

[0613] When the carbazole portion in the compound of Formula 1 is deuterated, that is, c1 in Formula 1b=a positive integer and c2 / c3=0, the light emitting properties of the organic light emitting device are further improved.

[0614] [synthesis]

[0615] 1. Synthesis of intermediates

[0616] (1) Intermediate 1

[0617]

[0618] 8.9 g (25 mmol) of 4-chloro-9,9-diphenyl-9H-fluorene was dissolved in 158 mL of D 2 O, 15.8 mL IPA and 316.4 mL decalin were added to a mixed solution, and then 5% Pt / C (3.36 g) was added. The solution was stirred at 100° C. for 24 hours in a high pressure reactor and then cooled to room temperature. Then, dichloromethane was added to separate the organic layer, and MgSO 4The separated organic layer was dried. The residual solution was concentrated. After adding IPA to the concentrated solution, the precipitated material was filtered to obtain Intermediate 1 (8 g). (Yield 86%)

[0619] (2) Intermediate 2

[0620]

[0621] After dissolving 24.2 g of 4-bromobiphenyl-d9 in 150 mL of toluene, 29.6 g of 1,1-diphenylformimine was added. 42.8 g of t-BuONa, 9.25 g of BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) and 6.80 g of Pd were added in sequence. 2 (dba) 3 The solution was allowed to react at 80°C for 6 hours under nitrogen. Then, 3N HCl was added to the reaction solution, and then reacted at 50°C for 4 hours under nitrogen. After the reaction was completed, the solution was filtered, and the organic layer was separated. Using MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 2 (8.3 g). (Yield 57%)

[0622] (3) Intermediate 3

[0623]

[0624] After dissolving 4.9 g of 4-bromobiphenyl-d9 in 60 mL of toluene, 2.5 g of intermediate 6 was added. 1.9 g of t-BuONa, 0.4 g of (t-Bu) 3 P and 0.8 g Pd 2 (dba) 3 The solution was reacted at 90°C. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 3 (2.7 g). (Yield 40%)

[0625] (4) Intermediate 4

[0626]

[0627] 8.8 g (25 mmol) of 5-chloro-9,9'-spirobifluorene was dissolved in 160 mL of D 2O, 16 mL IPA and 320 mL decalin were added to a mixed solution, and then 5% Pt / C (3.36 g) was added. The solution was stirred at 100°C for 24 hours in a high pressure reactor and then cooled to room temperature. Then, dichloromethane was added to separate the organic layer, and MgSO 4 The separated organic layer was dried. The residual solution was concentrated. After adding IPA to the concentrated solution, the precipitated material was filtered to obtain Intermediate 4 (7.9 g). (Yield 86%)

[0628] (5) Aniline-D5

[0629]

[0630] After dissolving 16.2 g of bromobenzene-d5 in 120 mL of toluene, 19.9 g of 1,1-diphenylformimine was added. Then, 28.8 g of t-BuONa, 6.23 g of BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) and 4.58 g of Pd were added in sequence. 2 (dba) 3 The solution was allowed to react at 80°C for 6 hours under nitrogen. Then, 3N HCl was added to the reaction solution, and then reacted at 50°C for 4 hours under nitrogen. After the reaction was completed, the solution was filtered, and the organic layer was separated. Using MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain aniline-d5 (5.6 g). (Yield 57%)

[0631] (6) Intermediate 5

[0632]

[0633] After dissolving 5.6 g of aniline-d5 in 50 mL of dichloromethane (MC), 8.21 g of Br 2 , and then react for 4 hours while slowly warming to room temperature. After the reaction was complete, 10 mL of 2M Na 2 S 2 O 3 After the organic layer was separated from the mixed layer, 10% Na 2 CO 3 10 mL of aqueous solution and distilled water were used to wash the material. After separation of the organic layer, MgSO 4 The water in the organic layer was removed. After the organic solution was concentrated, excess methanol was added to precipitate the product, and the product was filtered to obtain intermediate 5 (4.1 g). (Yield 41%)

[0634] (7) Intermediate 6

[0635]

[0636] After dissolving 5.4 g of bromobenzene-d5 in 80 mL of 1,4-dioxane, 9.3 g of bis(pinacolato)diboron was added. Then, 4.24 g of LiCl, 1.6 g of XPhos, and 0.38 g of Pd(OAc) were added in sequence. 2 The solution was allowed to react at 90° C. for 18 hours under nitrogen. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 6 (6.2 g). (Yield 91%)

[0637] (8) Intermediate 7

[0638]

[0639] After intermediate 5 (4.1 g) was dissolved in 50 mL of toluene, intermediate 6 (5.1 g) was added. Then, 5 mL of water, 9.7 g of K 2 CO 3 , 5 mL ethanol and 1.35 g Pd(PPh 3 ) 4 The solution was allowed to react at 80° C. for 12 hours under nitrogen. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 7 (2.5 g). (Yield 61%)

[0640] (9) Intermediate 8

[0641]

[0642] After dissolving 24.2 g of 4-bromobiphenyl-d9 in 150 mL of toluene, 29.6 g of 1,1-diphenylformimine was added. Then, 42.8 g of t-BuONa, 9.25 g of BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) and 6.80 g of Pd were added in sequence. 2 (dba) 3 The solution was allowed to react at 80°C for 6 hours under nitrogen. Then, 3N HCl was added to the reaction solution, and then reacted at 50°C for 4 hours under nitrogen. After the reaction was completed, the solution was filtered, and the organic layer was separated. Using MgSO 4The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 8 (8.3 g). (Yield 57%)

[0643] (10) Intermediate 9

[0644]

[0645] After dissolving 4.88 g of 4-bromobiphenyl-d9 in 60 mL of toluene, 2.54 g of intermediate 7 was added. Then, 1.86 g of t-BuONa, 0.35 g of (t-Bu) 3 P and 0.82 g Pd 2 (dba) 3 The solution was reacted at 90°C. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 9 (2.66 g). (Yield 40%)

[0646] (11) Intermediate 10

[0647]

[0648] Dissolve 6.8 g of 2-bromo-9,9'-dimethylfluorene in 137 mL of D 2 O, 14 mL IPA and 273 mL decalin were added to a mixed solution, and then 5% Pt / C (2.9 g) was added. The solution was stirred at 100°C for 24 hours in a high pressure reactor and then cooled to room temperature. Then, dichloromethane was added to separate the organic layer, and MgSO 4 The separated organic layer was dried. The residual solution was concentrated. After adding IPA to the concentrated solution, the precipitated material was filtered to obtain Intermediate 10 (6.15 g). (Yield 86%)

[0649] (12) Intermediate 11

[0650]

[0651] After the intermediate 10 (3 g) was dissolved in 40 mL of toluene, 1.50 g of the intermediate 8 was added. Then, 1.1 g of t-BuONa, 0.21 g of (t-Bu) 3 P and 0.48 g Pd 2 (dba) 3 The solution was reacted at 90°C. After the reaction, the solution was filtered and the organic layer was separated. MgSO 4The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain Intermediate 11 (1.66 g). (Yield 40%)

[0652] 2. Synthesis of EBL compounds

[0653] (1) Compound EBL1-1

[0654]

[0655] After the intermediate 1 (5.61 g) was dissolved in 60 mL of toluene, 6.51 g of N-(4-biphenyl)-4-benzidine was added. Then, 4.38 g of t-BuONa, 0.31 g of (t-Bu) 3 P and 0.69gPd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL1-1 (3.82 g). (Yield 39%)

[0656] (2) Compound EBL1-2

[0657]

[0658] After 5.35 g of 4-chloro-9,9-diphenyl-9H-fluorene was dissolved in 60 mL of toluene, Intermediate 3 (6.87 g) was added. Then, 4.38 g of t-BuONa, 0.31 g of (t-Bu) 3 P and 0.69 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 Water was removed from the separated organic layer. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL1-2 (3.83 g).

[0659] (yield 39%)

[0660] (3) Compounds EBL1-3

[0661]

[0662] After the intermediate 1 (5.61 g) was dissolved in 60 mL of toluene, the intermediate 3 (6.87 g) was added. Then, 4.38 g of t-BuONa, 0.31 g of (t-Bu) 3 P and 0.69 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL1-3 (3.94 g). (Yield 39%)

[0663] (4) Compound EBL7-1

[0664]

[0665] After the intermediate 4 (6.26 g) was dissolved in 60 mL of toluene, 4.63 g of N-(4-biphenyl)-2-benzidine was added. Then, 4.38 g of t-BuONa, 0.31 g of (t-Bu) 3 P and 0.69gPd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL7-1 (3.78 g). (Yield 34%)

[0666] (5) Compound EBL7-2

[0667]

[0668] After 7 g of 4-chloro-9,9'-spirobifluorene was dissolved in 60 mL of toluene, intermediate 9 (5.70 g) was added. Then, 5.11 g of t-BuONa, 0.36 g of (t-Bu) 3 P and 0.88 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL7-2 (4.57 g). (Yield 35%)

[0669] (6) Compound EBL7-3

[0670]

[0671] After intermediate 4 (7.3 g) was dissolved in 60 mL of toluene, intermediate 9 (5.70 g) was added. Then, 5.11 g of t-BuONa, 0.36 g of (t-Bu) 3 P and 0.88 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL7-3 (4.67 g). (Yield 35%)

[0672] (7) Compound EBL9-1

[0673]

[0674] After the intermediate 4 (7.3 g) was dissolved in 60 mL of toluene, 6.07 g of N-(4-biphenyl)-9,9'-dimethyl-9H-fluoren-2-amine was added. Then, 5.11 g of t-BuONa, 0.36 g of (t-Bu) 3 P and 0.88 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL9-1 (4.82 g). (Yield 35%)

[0675] (8) Compound EBL9-2

[0676]

[0677] After 7 g of 4-chloro-9,9'-spirobifluorene was dissolved in 60 mL of toluene, the intermediate 11 (6.44 g) was added. Then, 5.11 g of t-BuONa, 0.36 g of (t-Bu) 3 P and 0.88 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL9-2 (4.87 g). (Yield 35%)

[0678] (9)EBL9-3

[0679]

[0680] After the intermediate 4 (7.3 g) was dissolved in 60 mL of toluene, the intermediate 11 (6.44 g) was added. Then, 5.11 g of t-BuONa, 0.36 g of (t-Bu) 3 P and 0.88 g Pd 2 (dba) 3 The solution was refluxed and stirred under nitrogen to react. After the reaction was completed, the solution was filtered and the organic layer was separated. MgSO 4 The water in the separated organic layer was removed. The organic layer was separated by column chromatography to separate the product. The separated product was purified by recrystallization to obtain compound EBL9-3 (4.98 g). (Yield 35%)

[0681] The third compound 316 as a dopant in the green light emitting EML 303 (eg, green EML) may be represented by Formula 12.

[0682] [Formula 12]

[0683]

[0684] In Formula 12, each of R61, R62, R63 and R64 is independently selected from the group consisting of substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl. In addition, each of e1, e2, e3 and e4 is independently an integer from 0 to 4, and n is an integer from 1 to 3.

[0685] For example, the compound of Formula 12 can be one of the compounds of Formula 13.

[0686] [Formula 13]

[0687]

[0688] That is, the green EML 303 may include the first compound 312 of Formula 1 as an N-type host, the second compound 314 of Formula 2 as a P-type host, and the third compound 316 of Formula 12 as a dopant or an emitter.

[0689] In the green EML 303, the weight % of each of the first compound 312 and the second compound 314 may be greater than the weight % of the third compound 316, and the weight % of the first compound 312 may be the same as or different from the weight % of the second compounds 312 and 314. In the green EML 303, the weight % of the second compound 314 may be greater than the weight % of the first compound 312. In the green EML 303, the weight % of the third compound 316 may be 1% to 25%, preferably 5% to 10%.

[0690] For example, the organic light emitting layer (e.g., organic material layer) may include an EML (light emitting layer) between an anode and a cathode, an HTL between the anode and the EML, an EBL between the HTL and the EML, and an ETL between the EML and the cathode. In this case, the EML may contact the EBL and the ETL. That is, the organic light emitting layer may include the EBL but not the HBL.

[0691] In addition, the organic light emitting layer may further include at least one of a HIL positioned between the anode and the HTL, and an EIL positioned between the cathode and the ETL.

[0692] The EML includes the compound of Formula 1 as a first compound (eg, an N-type body) and the compound of Formula 2 as a second compound (eg, a P-type body), and the EBL adjacent to the EML includes the compound of Formula 10.

[0693] In this case, at least one hydrogen in the compound of formula 10 is deuterated. That is, the compound of formula 10 may be partially deuterated or completely deuterated. For example, only the fluorene portion of the spirofluorene portion in formula 10 may be deuterated. In addition, each of the first compound of formula 1 and the second compound of formula 2 may be non-deuterated, partially deuterated or completely deuterated. For example, the first compound of formula 1 has a first deuteration rate, and the second compound of formula 2 has a second deuteration rate that is less than the first deuteration rate. That is, in combination with an EBL comprising a partially or completely deuterated compound of formula 10, the deuteration rate of the first compound is greater than the deuteration rate of the second compound.

[0694] In an organic light emitting diode (OLED, such as an organic light emitting device) having the above structure and configuration, the driving voltage is reduced and the life span is significantly increased. In addition, when only the fluorene part of the spirofluorene part in Formula 10 is deuterated, the life span and driving performance of the OLED can be improved while minimizing the increase in production cost due to deuterium atoms. In addition, when only the carbazole part or the fused carbazole part in Formula 1 is deuterated, the life span and driving performance of the OLED can be improved, and the life span and driving performance of the OLED can be improved while further minimizing the increase in production cost due to deuterium atoms.

[0695] Figure 5is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure.

[0696] like Figure 5 As shown, the organic light emitting display device 500 includes a substrate 510, a TFT Tr, and an OLED D (e.g., an organic light emitting device) connected to the TFT Tr. For example, the organic light emitting display device 500 may include a red pixel, a green pixel, and a blue pixel, and the OLED D may be formed in each of the red pixel, the green pixel, and the blue pixel. That is, the OLED D emitting red light, green light, and blue light may be respectively disposed in the red pixel, the green pixel, and the blue pixel.

[0697] The substrate 510 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be one of a polyimide (PI) substrate, polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and polycarbonate (PC).

[0698] The buffer layer 520 is formed on the substrate, and the TFT Tr is formed on the buffer layer 520. The buffer layer 520 may be omitted.

[0699] The semiconductor layer 522 is formed on the buffer layer 520. The semiconductor layer 522 may include an oxide semiconductor material or polysilicon.

[0700] When the semiconductor layer 522 includes an oxide semiconductor material, a light shielding pattern (not shown) may be formed under the semiconductor layer 522. Light reaching the semiconductor layer 522 is shielded or blocked by the light shielding pattern, thereby preventing thermal degradation of the semiconductor layer 522. On the other hand, when the semiconductor layer 522 includes polysilicon, impurities may be doped into both sides of the semiconductor layer 522.

[0701] The gate insulating layer 524 is formed on the semiconductor layer 522. The gate insulating layer 524 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0702] The gate electrode 530 formed of a conductive material such as metal is formed on the gate insulating layer 524 to correspond to the center of the semiconductor layer 522 .

[0703] exist Figure 5 In the embodiment of the present invention, the gate insulating layer 524 is formed on the entire surface of the substrate 510. Alternatively, the gate insulating layer 524 may be patterned to have the same shape as the gate electrode 530.

[0704] An interlayer insulating layer 532 formed of an insulating material is formed on the gate electrode 530. The interlayer insulating layer 532 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo acryl.

[0705] The interlayer insulating layer 532 includes a first contact hole 534 and a second contact hole 536 exposing both sides of the semiconductor layer 522. The first contact hole 534 and the second contact hole 536 are located at both sides of the gate electrode 530 to be spaced apart from the gate electrode 530.

[0706] The first contact hole 534 and the second contact hole 536 are formed through the gate insulating layer 524. Alternatively, when the gate insulating layer 524 is patterned to have the same shape as the gate electrode 530, the first contact hole 534 and the second contact hole 536 are formed through only the interlayer insulating layer 532.

[0707] A source electrode 540 and a drain electrode 542 formed of a conductive material such as metal are formed on the interlayer insulating layer 532 .

[0708] The source electrode 540 and the drain electrode 542 are spaced apart from each other with respect to the gate electrode 530 , and contact both sides of the semiconductor layer 522 through the first contact hole 534 and the second contact hole 536 , respectively.

[0709] The semiconductor layer 522, the gate electrode 530, the source electrode 540, and the drain electrode 542 constitute a TFT Tr. The TFT Tr functions as a driving element.

[0710] In the TFT Tr, a gate electrode 530, a source electrode 540, and a drain electrode 542 are located above the semiconductor layer 522. That is, the TFT Tr has a coplanar structure.

[0711] Alternatively, in the TFT Tr, the gate electrode may be located below the semiconductor layer, and the source electrode and the drain electrode may be located above the semiconductor layer, so that the TFT Tr may have an inverse staggered structure. In this case, the semiconductor layer may include amorphous silicon.

[0712] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0713] In addition, a power line and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed. The power line may be formed parallel to and spaced apart from one of the gate line and the data line.

[0714] The planarization layer 550 is formed to cover the TFT Tr, and the planarization layer 550 includes a drain contact hole 552 exposing the drain electrode 542 of the TFT Tr.

[0715] A first electrode 200 is formed in each pixel region and on the planarization layer 550, respectively, and the first electrode 200 is connected to the drain electrode 542 of the TFT Tr via the drain contact hole 552. The first electrode 200 may be an anode and may be formed of a conductive material having a relatively high work function. For example, the first electrode 200 may be formed of a transparent conductive material such as indium tin oxide (ITO) or indium zinc oxide (IZO).

[0716] When the organic light-emitting display device 500 operates in a bottom emission type, the first electrode 200 may have a single-layer structure of a transparent conductive material layer. Alternatively, when the organic light-emitting display device 500 operates in a top emission type, the first electrode 200 may further include a reflective layer. For example, the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In a top emission type organic light-emitting display device 500, the first electrode 200 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0717] The bank layer 566 is formed on the planarization layer 550 to cover the edge of the first electrode 200. That is, the bank layer 566 is located at the boundary of the pixel and exposes the center of the first electrode 200 in the pixel region.

[0718] The organic light emitting layer 300 is formed on the first electrode 200. The organic light emitting layer 300 is formed in each of the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0719] In the green pixel region, the organic light emitting layer 300 may include a single light emitting portion including an EML.

[0720] For example, refer to Figure 3 The organic light emitting layer 300 may include an EML 303, a HIL 301 located below the EML 303, a HTL 302 located between the EML 303 and the HIL 301, an EBL 307 located between the EML 303 and the HTL 302, an EIL 306 located above the EML 303, an ETL 305 located between the EML 303 and the EIL 306, and a HBL 304 located between the EML 303 and the ETL 305.

[0721] Alternatively, the HBL 304 may be omitted. In this case, one side of the EML 303 contacts the EBL 307 , and the other side of the EML 303 contacts the ETL 305 .

[0722] The EML 303 may include a compound of Formula 1 as a first compound 312 (eg, an N-type host), a compound of Formula 2 as a second compound 314 (eg, a P-type host), and a compound of Formula 12 as a third compound 316 (eg, a dopant or an emitter).

[0723] In addition, the EBL 307 may include the compound of Formula 10 as the electron blocking material 322 .

[0724] Alternatively, the organic light emitting layer 300 may include a plurality of light emitting portions, each of which includes the EML.

[0725] Reference Figure 6 , which is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure, the organic light-emitting layer 300 includes a first light-emitting portion 610 including a first green EML 620 and a second light-emitting portion 640 including a second green EML 650. The organic light-emitting layer 300 may further include a charge generation layer (CGL) 670 located between the first light-emitting portion 610 and the second light-emitting portion 640.

[0726] The first light emitting portion 610 may further include a first EBL 630 between the first green EML 620 and the first electrode 200 .

[0727] In addition, the first light emitting portion 610 may further include a first HTL 614 between the first EML 630 and the first electrode 200 and a first ETL 616 between the first green EML 620 and the second light emitting portion 640. For example, the first ETL 616 may be located between the first green EML 620 and the CGL 670.

[0728] In addition, the first light emitting portion 610 may further include a HIL 612 between the first HTL 614 and the first electrode 200 .

[0729] The second light emitting portion 640 may further include a second EBL 660 between the second green EML 650 and the first light emitting portion 610 .

[0730] In addition, the second light emitting portion 640 may further include a second HTL 642 between the second EBL 660 and the first light emitting portion 610 , and a second ETL 644 between the second green EML 650 and the second electrode 400 .

[0731] In addition, the second light emitting portion 640 may further include an EIL 646 located between the second ETL 644 and the second electrode 400 .

[0732] The CGL 670 is located between the first light emitting portion 610 and the second light emitting portion 640. That is, the first light emitting portion 610 and the second light emitting portion 640 are connected through the CGL 670. The CGL 670 may be a PN junction CGL of an N-type CGL 672 and a P-type CGL 674.

[0733] The N-type CGL 672 is located between the first ETL 616 and the second HTL 642 , and the P-type CGL 674 is located between the N-type CGL 672 and the second HTL 642 .

[0734] The first green EML 620 includes a first compound 622 , a second compound 624 , and a third compound 626 , and the second green EML 650 includes a fourth compound 652 , a fifth compound 654 , and a sixth compound 656 .

[0735] In the first green EML 620, the first compound 622 may be an N-type host, such as a first host, the second compound 624 may be a P-type host, such as a second host, and the third compound 626 may be an emitter, such as a dopant. In the second green EML 650, the fourth compound 652 may be an N-type host, such as a first host, the fifth compound 654 may be a P-type host, such as a second host, and the sixth compound 656 may be an emitter, such as a dopant.

[0736] At least one of the first compound 622 and the fourth compound 652 is a compound of Formula 1, and at least one of the second compound 624 and the fifth compound 654 is a compound of Formula 2. In addition, at least one of the third compound 626 and the sixth compound 656 is a compound of Formula 12.

[0737] For example, the first compound 622 and the fourth compound 652 are compounds of Formula 1 and are the same or different. The second compound 624 and the fifth compound 654 are compounds of Formula 2 and are the same or different. The third compound 626 and the sixth compound 656 are compounds of Formula 12 and are the same or different.

[0738] Each of the first compound 622 and the fourth compound 652 may be non-deuterated, partially deuterated, or fully deuterated. For example, a1 in Formula 1b may be a positive integer.

[0739] Each of the second compound 624 and the fifth compound 654 can be non-deuterated, partially deuterated, or fully deuterated.

[0740] For example, in the green EML 620 , the deuteration rate of the first compound 622 may be greater than the deuteration rate of the second compound 624 . Also, in the green EML 650 , the deuteration rate of the fourth compound 652 may be greater than the deuteration rate of the fifth compound 654 .

[0741] In the green EML 620, the weight % of the second compound 624 may be less than that of the first compound 622 and may be greater than that of the third compound 626. In addition, in the green EML 650, the weight % of the fifth compound 654 may be less than that of the fourth compound 652 and may be greater than that of the sixth compound 656.

[0742] The first EBL 630 includes a first electron blocking material 632, and the second EML 660 includes a second electron blocking material 662. Each of the first electron blocking material 632 and the second electron blocking material 662 is a compound of Formula 10. For example, the first electron blocking material 632 and the second electron blocking material 662 may be a compound of Formula 10 and may be the same or different.

[0743] Each of the first electron blocking material 632 and the second electron blocking material 662 may be partially deuterated or fully deuterated. That is, at least one of c1, c2, and c3 in Formula 10 may be a positive integer. For example, when only the fluorene portion or the spirofluorene portion is deuterated, that is, c1=positive integer and c2=c3=0, the lifetime and driving performance of the device may be improved while minimizing the increase in production cost due to deuterium atoms.

[0744] Reference Figure 5 , the second electrode 400 is formed above the substrate 510 including the organic light emitting layer 300. The second electrode 400 may be disposed over the entire surface of the display area and may be formed of a conductive material having a relatively low work function to serve as a cathode. For example, the second electrode 400 may be formed of one of aluminum (Al), magnesium (Mg), silver (Ag) and alloys thereof (e.g., Al-Mg alloy (AlMg) or Ag-Mg alloy (MgAg)). In a top emission type OLED, the second electrode 400 has a thin profile so as to be transparent (or translucent).

[0745] The first electrode 200 , the organic light emitting layer 300 , and the second electrode 400 constitute an OLED D.

[0746] An encapsulation film (or encapsulation layer) 570 is formed on the second electrode 400 to prevent moisture from penetrating into the OLED D. The encapsulation film 570 includes a first inorganic insulating layer 572, an organic insulating layer 574, and a second inorganic insulating layer 576 sequentially stacked, but is not limited thereto. The encapsulation film 570 may be omitted.

[0747] The organic light-emitting display device 500 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emitting organic light-emitting display device 500, the polarizing plate may be disposed below the substrate 510. In a top-emitting organic light-emitting display device 500, the polarizing plate may be disposed on or above the encapsulation film 570.

[0748] In addition, in the top emission type organic light emitting display device 500, a cover window (not shown) may be attached to the packaging film 570 or the polarizing plate. In this case, the substrate 510 and the cover window have flexible characteristics, so that a flexible organic light emitting display device can be provided.

[0749] Figure 7 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure. Figure 8 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure, Fig. 9 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present disclosure.

[0750] like Figure 7 As shown, the organic light emitting display device 700 includes: a first substrate 710, in which red pixels RP, green pixels GP and blue pixels BP are defined; a second substrate 770 facing the first substrate 710; an OLED D, which is located between the first substrate 710 and the second substrate 770 and provides white light emission; and a color filter layer 780 located between the OLED D and the second substrate 770.

[0751] Each of the first substrate 710 and the second substrate 770 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be one of a polyimide (PI) substrate, polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and polycarbonate (PC).

[0752] The buffer layer 720 is formed on the first substrate, and the TFT Tr corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP is formed on the buffer layer 720. The buffer layer 720 may be omitted.

[0753] The semiconductor layer 722 is formed on the buffer layer 720. The semiconductor layer 722 may include an oxide semiconductor material or polysilicon.

[0754] The gate insulating layer 724 is formed on the semiconductor layer 722. The gate insulating layer 724 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0755] The gate electrode 730 formed of a conductive material such as metal is formed on the gate insulating layer 724 to correspond to the center of the semiconductor layer 722 .

[0756] An interlayer insulating layer 732 formed of an insulating material is formed on the gate electrode 730. The interlayer insulating layer 732 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo acryl.

[0757] The interlayer insulating layer 732 includes a first contact hole 734 and a second contact hole 736 exposing both sides of the semiconductor layer 722. The first contact hole 734 and the second contact hole 736 are located at both sides of the gate electrode 730 to be spaced apart from the gate electrode 730.

[0758] A source electrode 740 and a drain electrode 742 formed of a conductive material such as metal are formed on the interlayer insulating layer 532 .

[0759] The source electrode 740 and the drain electrode 742 are spaced apart from each other with respect to the gate electrode 730 , and contact both sides of the semiconductor layer 722 through the first contact hole 734 and the second contact hole 736 , respectively.

[0760] The semiconductor layer 722, the gate electrode 730, the source electrode 740, and the drain electrode 742 constitute a TFT Tr. The TFT Tr functions as a driving element.

[0761] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0762] In addition, a power line and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed. The power line may be formed parallel to and spaced apart from one of the gate line and the data line.

[0763] The planarization layer 750 is formed to cover the TFT Tr, and includes a drain contact hole 752 exposing the drain electrode 742 of the TFT Tr.

[0764] A first electrode 200 is formed in each pixel and on the planarization layer 750, respectively, and the first electrode 200 is connected to the drain electrode 742 of the TFT Tr via the drain contact hole 752. The first electrode 200 may be an anode and may be formed of a conductive material having a relatively high work function (e.g., a transparent conductive oxide (TCO)). The first electrode 200 may further include a reflective electrode or a reflective layer. For example, the reflective electrode or the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emitting organic light-emitting display device 700, the first electrode 200 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0765] The bank layer 766 is formed on the planarization layer 750 to cover the edge of the first electrode 760. That is, the bank layer 766 is located at the boundary of the pixel and exposes the center of the first electrode 200 in the pixel. Since the OLED D emits white light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light emitting layer 300 may be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without separation. The bank layer 766 may be formed to prevent current leakage at the edge of the first electrode 760, and may be omitted.

[0766] The organic light emitting layer 762 is formed on the first electrode 200 .

[0767] Reference Figure 8 , the organic light emitting layer 300 includes a first light emitting portion 830 including a green EML 810a, a second light emitting portion 840 including a first blue EML 850, and a third light emitting portion 860 including a second blue EML 870. In addition, the organic light emitting layer 300 may further include a first CGL 880 located between the first light emitting portion 830 and the second light emitting portion 840, and a second CGL 890 located between the first light emitting portion 830 and the third light emitting portion 860. In addition, the first light emitting portion 830 may further include a red EML 810b.

[0768] The second light emitting portion 840 is located between the first electrode 200 and the first light emitting portion 830, and the third light emitting portion 860 is located between the first light emitting portion 830 and the second electrode 400. In addition, the second light emitting portion 840 is located between the first electrode 200 and the first CGL 880, and the third light emitting portion 860 is located between the second CGL 890 and the second electrode 400. That is, the second light emitting portion 840, the first CGL 880, the first light emitting portion 830, the second CGL 890, and the third light emitting portion 860 are sequentially stacked on the first electrode 200.

[0769] In the first light emitting portion 830 , the red EML 810 a may be located below the green EML 810 a .

[0770] The first light emitting portion 830 may further include an EBL 820 located under the red EML 810 b .

[0771] In addition, the first light emitting portion 830 may further include a first ETL 834 located above the green EML 810 a and a first HTL 832 located below the EBL 820 .

[0772] For example, in the first light emitting portion 830 , the EBL 820 may be located between the red EML 810 b and the first HTL 832 , and the green EML 810 a may be located between the red EML 810 b and the first ETL 834 .

[0773] The second light emitting portion 840 may further include at least one of a second HTL 844 located below the first blue EML 850 and a second ETL 846 located above the first blue EML 850. In addition, the second light emitting portion 840 may further include a HIL 842 located between the first electrode 200 and the second HTL 844.

[0774] In addition, the second light emitting portion 840 may further include at least one of an EBL (not shown) located between the second HTL 844 and the first blue EML 850 , and an HBL (not shown) located between the second ETL 846 and the first blue EML 850 .

[0775] The third light emitting portion 860 may further include at least one of a third HTL 862 located below the second blue EML 870 and a third ETL 864 located above the second blue EML 870. In addition, the third light emitting portion 860 may further include an EIL 866 located between the second electrode 400 and the third ETL 864.

[0776] In addition, the third light emitting portion 860 may further include at least one of an EBL (not shown) located between the third HTL 862 and the second blue EML 870 and an HBL (not shown) located between the third ETL 864 and the second blue EML 870 .

[0777] Green EML 810a includes a first compound 812, a second compound 814, and a third compound 816. The first compound 812 may be an N-type host, such as a first host, the second compound 814 may be a P-type host, such as a second host, and the third compound 816 may be an emitter, such as a dopant.

[0778] The first compound 812 is a compound of Formula 1, and the second compound 814 is a compound of Formula 2. In addition, the third compound 816 is a compound of Formula 12.

[0779] The first compound 812 may be non-deuterated, partially deuterated, or fully deuterated. For example, a1 in Formula 1b may be a positive integer.

[0780] The second compound 814 can be non-deuterated, partially deuterated, or fully deuterated.

[0781] For example, in the green EML 810 a , the deuteration rate of the first compound 812 may be greater than the deuteration rate of the second compound 814 .

[0782] In the green EML 810 , a weight % of the second compound 814 may be less than a weight % of the first compound 812 and may be greater than a weight % of the third compound 816 .

[0783] In the first light emitting portion 830, the EBL 820 includes an electron blocking material 822. The electron blocking material 822 is a compound of Formula 10.

[0784] The electron blocking material 822 may be partially deuterated or fully deuterated. That is, at least one of c1, c2, and c3 in Formula 10 may be a positive integer. For example, when only the fluorene portion or the spirofluorene portion is deuterated, that is, c1=positive integer and c2=c3=0, the lifetime and driving performance of the device may be improved while minimizing the increase in production cost due to deuterium atoms.

[0785] The red EML 810b may include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 810b, the red host may have a weight % greater than the red dopant. In the red EML 810b, the red dopant may be doped at 1 to 10, preferably 1 to 5 weight %.

[0786] For example, the red host can be selected from the group consisting of: 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), CBP, 1,3,5-tri(carbazole-9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (Spiro-CBP), D PEPO, 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCzl), bis(2-hydroxyphenyl)-pyridine)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinoline)beryllium (Bebq2), and 1,3,5-tri(1-pyrenyl)benzene (TPB3), but are not limited thereto.

[0787] In addition, the red dopant may be selected from the group consisting of: bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dioic acid)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III) (Hex-Ir(phq) 2 (acac)), tris[2-(4-n-hexylphenyl)quinolinol]iridium(III) (Hex-Ir(phq) 3 )、Tris[2-phenyl-4-methylquinoline]iridium(III) (Ir(Mphq) 3 ), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dicarboxylate)iridium(III)(Ir(dpm)PQ 2 ), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dicarboxylate)iridium(III)(Ir(dpm)(piq) 2 ), bis[(4-n-hexylphenyl)isoquinolinol](acetylacetonate)iridium(III) (Hex-Ir(piq) 2 (acac)), tris[2-(4-n-hexylphenyl)quinolinol]iridium(III) (Hex-Ir(piq) 3 ), tris(2-(3-methylphenyl)-7-methyl-quinolinol)iridium (Ir(dmpq) 3 ), bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium(III) (Ir(dmpq) 2 (acac)), and bis[2-(3,5-dimethylphenyl)-4-methyl-quinolinol](acetylacetonate)iridium(III) (Ir(mphmq)2 (acac)), but not limited to.

[0788] The first blue EML 850 in the second light emitting portion 840 includes a first blue host and a first blue dopant, and the second blue EML 870 in the third light emitting portion 860 includes a second blue host and a second blue dopant.

[0789] Each of the first blue dopant and the second blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the first blue EML 850, the first blue host may have a weight % greater than that of the first blue dopant. In the second blue EML 870, the second blue host may have a weight % greater than that of the second blue dopant. In each of the first blue EML 850 and the second blue EML 870, each of the first blue dopant and the second blue dopant may be doped at 1 to 10, preferably 1 to 5, weight %.

[0790] For example, each of the first blue host and the second blue host can be independently selected from the group consisting of: mCP, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), mCBP, CBP-CN, 9-(3-(9H-carbazole-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole (mCPPO1), 3,5-di(9H-carbazole-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3' ...

[0045] The invention relates to bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirobisfluoro-2-yl-diphenyl-phosphine oxide (SPPO1), and 9,9'-(5-(triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (SimCP), but is not limited thereto.

[0791] Each of the first blue dopant and the second blue dopant may be independently selected from the group consisting of perylene, 4,4′-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4-4′-[(di-p-tolylamino)phenylvinyl]stilbene (DPAVB), 4,4′-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 2,7-bis(4-diphenylamino)phenylvinyl)-9,9-spirofluorene (spiro-DPVBi), [1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene (DSB), 1-4-bis-[4-(N,N-diphenylamino)phenylvinyl]benzene (DSB), A), 2,5,8,11-tetra-tetrabutylperylene (TBPe), bis(2-hydroxyphenyl)-pyridinyl) beryllium (Bepp2), 9-(9-phenylcarbazole-3-yl)-10-(naphthalene-1-yl) anthracene (PCAN), mer-tris(1-phenyl-3-methylimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ) (mer-Ir(pmi)3), fac-tris(1,3-diphenyl-benzimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ) (fac-Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridinyl)phenyl-(2-carboxypyridinyl)iridium(Ⅲ) (Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine))iridium(Ⅲ) (Ir(Fppy) 3 ), and bis[2-(4,6-difluorophenyl)pyridine-C2,N](picolinate)iridium(III) (FIrpic), but are not limited thereto.

[0792] For example, each of the first blue EML 850 and the second blue EML 870 may include an anthracene derivative as a host and a boron derivative as a dopant.

[0793] The first CGL 880 is located between the first light emitting portion 830 and the second light emitting portion 840, and the second CGL 890 is located between the first light emitting portion 830 and the third light emitting portion 860. That is, the first light emitting portion 830 and the second light emitting portion 840 are connected to each other through the first CGL 880, and the first light emitting portion 830 and the third light emitting portion 860 are connected to each other through the second CGL 890. The first CGL 880 may be a PN junction CGL of an N-type CGL 882 and a P-type CGL 884, and the second CGL 890 may be a PN junction CGL of an N-type CGL 892 and a P-type CGL 894.

[0794] The N-type CGL 882 of the first CGL 880 is located between the first HTL 832 and the second ETL 846 , and the P-type CGL 884 of the first CGL 880 is located between the N-type CGL 882 and the first HTL 832 .

[0795] The N-type CGL 892 of the second CGL 890 is located between the first ETL 834 and the third HTL 862 , and the P-type CGL 894 of the second CGL 890 is located between the N-type CGL 892 and the third HTL 862 .

[0796] As described above, the OLED D of the present disclosure includes the first light emitting portion 830 including the green EML 810a and the red EML 810b, the second light emitting portion 840 including the first blue EML 850, and the third light emitting portion 860 including the second blue EML 870, and provides white light emission.

[0797] The green EML 810a includes the compound of Formula 1 as the first compound 812 and the compound of Formula 2 as the second compound 814. Therefore, in the OLED D, the driving voltage is reduced, and the light emitting efficiency and lifespan are improved.

[0798] In addition, the first light emitting portion 830 including the green EML 810a includes the EBL 820, and the EBL 820 includes the compound of Formula 10 as the electron blocking material 822. Therefore, in the OLED D, the driving voltage is further reduced, and the light emitting efficiency and the lifespan are further improved.

[0799] Reference Fig. 9 , the organic light emitting layer 300 includes: a first light emitting portion 930 including a green EML 910a, a red EML 910b, and a yellow-green EML 910c; a second light emitting portion 940 including a first blue EML 950; and a third light emitting portion 960 including a second blue EML 970. In addition, the organic light emitting layer 300 may further include a first CGL 980 located between the first light emitting portion 930 and the second light emitting portion 940, and a second CGL 990 located between the first light emitting portion 930 and the third light emitting portion 960.

[0800] The second light emitting portion 940 is located between the first electrode 200 and the first light emitting portion 930, and the third light emitting portion 960 is located between the first light emitting portion 930 and the second electrode 400. In addition, the second light emitting portion 940 is located between the first electrode 200 and the first CGL 980, and the third light emitting portion 960 is located between the second CGL 990 and the second electrode 400. That is, the second light emitting portion 940, the first CGL 980, the first light emitting portion 930, the second CGL 990, and the third light emitting portion 960 are sequentially stacked on the first electrode 200.

[0801] In the first light emitting portion 930, the red EML 910a may be located below the yellow-green EML 910c, and the green EML 910a may be located above the yellow-green EML 910c. Figure 8 The first light emitting portion 830 of the OLED D includes an EML having a double-layer structure of a green EML 810a and a red EML 810b, and Fig. 9 The first light emitting portion 930 of the OLED D includes an EML having a three-layer structure of a green EML 910a, a red EML 910b, and a yellow-green EML 910c.

[0802] The first light emitting portion 930 may further include an EBL 920 located under the red EML 910 b .

[0803] In addition, the first light emitting portion 930 may further include a first ETL 934 located above the green EML 910 a and a first HTL 932 located below the EBL 920 .

[0804] For example, in the first light emitting portion 930 , the red EML 910 b may be located between the EBL 920 and the yellow-green EML 910 c , and the green EML 910 a may be located between the yellow-green EML 910 c and the first ETL 934 .

[0805] The second light emitting portion 940 may further include at least one of a second HTL 944 located below the first blue EML 950 and a second ETL 946 located above the first blue EML 950. In addition, the second light emitting portion 940 may further include a HIL 942 located between the first electrode 200 and the second HTL 944.

[0806] In addition, the second light emitting portion 940 may further include at least one of an EBL (not shown) located between the second HTL 944 and the first blue EML 950 , and an HBL (not shown) located between the second ETL 946 and the first blue EML 950 .

[0807] The third light emitting portion 960 may further include at least one of a third HTL 962 located below the second blue EML 970 and a third ETL 964 located above the second blue EML 970. In addition, the third light emitting portion 960 may further include an EIL 966 located between the second electrode 400 and the third ETL 964.

[0808] In addition, the third light emitting portion 960 may further include at least one of an EBL (not shown) located between the third HTL 962 and the second blue EML 970 and an HBL (not shown) located between the third ETL 964 and the second blue EML 970 .

[0809] The green EML 910a includes a first compound 912, a second compound 914, and a third compound 916. The first compound 912 may be an N-type host, such as a first host, the second compound 914 may be a P-type host, such as a second host, and the third compound 916 may be an emitter, such as a dopant.

[0810] The first compound 912 is a compound of Formula 1, and the second compound 914 is a compound of Formula 2. In addition, the third compound 916 is a compound of Formula 12.

[0811] The first compound 912 may be non-deuterated, partially deuterated, or fully deuterated. For example, a1 in Formula 1b may be a positive integer.

[0812] The second compound 914 can be non-deuterated, partially deuterated, or fully deuterated.

[0813] For example, in the green EML 910 a , the deuteration rate of the first compound 912 may be greater than the deuteration rate of the second compound 914 .

[0814] In the green EML 910 , a weight % of the second compound 914 may be less than a weight % of the first compound 912 and may be greater than a weight % of the third compound 916 .

[0815] In the first light emitting portion 930, the EBL 920 includes an electron blocking material 922. The electron blocking material 922 is a compound of Formula 10.

[0816] The electron blocking material 922 may be partially deuterated or fully deuterated. That is, at least one of c1, c2, and c3 in Formula 10 may be a positive integer. For example, when only the fluorene portion or the spirofluorene portion is deuterated, i.e., c1=positive integer and c2=c3=0, the lifetime and driving performance of the device may be improved while minimizing the increase in production cost due to deuterium atoms.

[0817] The red EML 910b may include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 910b, the red host may have a weight % greater than the red dopant. In the red EML 910b, the red dopant may be doped at 1 to 10, preferably 1 to 5 weight %.

[0818] The yellow-green EML 910c may include a yellow-green host and a yellow-green dopant. The yellow-green dopant may include at least one of a yellow-green phosphorescent compound, a yellow-green fluorescent compound, and a yellow-green delayed fluorescent compound. In the yellow-green EML 910c, the yellow-green host may have a weight percentage greater than that of the yellow-green dopant. In the yellow-green EML 910c, the yellow-green dopant may be doped at 1 to 10, preferably 1 to 5 weight %.

[0819] The first blue EML 950 in the second light emitting portion 940 includes a first blue host and a first blue dopant, and the second blue EML 970 in the third light emitting portion 960 includes a second blue host and a second blue dopant.

[0820] Each of the first blue dopant and the second blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the first blue EML 950, the first blue host may have a weight % greater than that of the first blue dopant. In the second blue EML 970, the second blue host may have a weight % greater than that of the second blue dopant. In each of the first blue EML 950 and the second blue EML 970, each of the first blue dopant and the second blue dopant may be doped at 1 to 10, preferably 1 to 5, weight %.

[0821] For example, each of the first blue EML 950 and the second blue EML 970 may include an anthracene derivative as a host and a boron derivative as a dopant.

[0822] The first CGL 980 is located between the first light emitting portion 930 and the second light emitting portion 940, and the second CGL 990 is located between the first light emitting portion 930 and the third light emitting portion 960. That is, the first light emitting portion 930 and the second light emitting portion 940 are connected to each other through the first CGL 980, and the first light emitting portion 930 and the third light emitting portion 960 are connected to each other through the second CGL 990. The first CGL 980 may be a PN junction CGL of an N-type CGL 982 and a P-type CGL 984, and the second CGL 990 may be a PN junction CGL of an N-type CGL 992 and a P-type CGL 994.

[0823] The N-type CGL 982 of the first CGL 980 is located between the first HTL 932 and the second ETL 946 , and the P-type CGL 984 of the first CGL 980 is located between the N-type CGL 982 and the first HTL 932 .

[0824] The N-type CGL 992 of the second CGL 990 is located between the first ETL 934 and the third HTL 962 , and the P-type CGL 994 of the second CGL 990 is located between the N-type CGL 992 and the third HTL 962 .

[0825] As described above, the OLED D of the present disclosure includes the first light emitting portion 930 including the green EML 910a, the red EML 910b, and the yellow-green EML 910c, the second light emitting portion 940 including the first blue EML 950, and the third light emitting portion 960 including the second blue EML 970, and provides white light emission.

[0826] The green EML 910a includes the compound of Formula 1 as the first compound 912 and the compound of Formula 2 as the second compound 914. Therefore, in the OLED D, the driving voltage is reduced, and the light emitting efficiency and lifespan are improved.

[0827] In addition, the first light emitting portion 930 including the green EML 910a includes the EBL 920, and the EBL 920 includes the compound of Formula 10 as the electron blocking material 922. Therefore, in the OLED D, the driving voltage is further reduced, and the light emitting efficiency and the lifespan are further improved.

[0828] Refer again Figure 7 , a second electrode 400 is formed on the substrate 410 on which the organic light emitting layer 300 is formed.

[0829] In the organic light emitting display device 700 , since light emitted from the organic light emitting layer 300 is incident to the color filter layer 780 through the second electrode 400 , the second electrode 400 has a thin profile for transmitting the light.

[0830] The first electrode 200 , the organic light emitting layer 300 , and the second electrode 400 constitute an OLED D.

[0831] The color filter layer 780 is located above the OLED D and includes a red color filter 782, a green color filter 784, and a blue color filter 786 corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. The red color filter 782 may include at least one of a red dye and a red pigment, the green color filter 784 may include at least one of a green dye and a green pigment, and the blue color filter 786 may include at least one of a blue dye and a blue pigment.

[0832] Although not shown, the color filter layer 480 may be attached to the OLED D by using an adhesive layer. Alternatively, the color filter layer 780 may be formed directly on the OLED D.

[0833] An encapsulation film (not shown) may be formed to prevent moisture from penetrating into the OLED D. For example, the encapsulation film may include a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer sequentially stacked, but is not limited thereto. The encapsulation film may be omitted.

[0834] A polarizing plate (not shown) for reducing ambient light reflection may be disposed above the top emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.

[0835] exist Figure 7 In the OLED D, the first electrode 200 and the second electrode 400 are respectively a reflective electrode and a transparent (or semi-transparent) electrode, and the color filter layer 780 is disposed above the OLED D. Alternatively, when the first electrode 200 and the second electrode 400 are respectively a transparent (or semi-transparent) electrode and a reflective electrode, the color filter layer 780 may be disposed between the OLED D and the first substrate 710.

[0836] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 780. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. White light emitted from the OLED D is converted into red light, green light, and blue light by the red conversion layer, the green conversion layer, and the blue conversion layer, respectively. For example, the color conversion layer may include quantum dots. Therefore, the color purity of the organic light emitting display device 700 can be further improved.

[0837] A color conversion layer may be included instead of the color filter layer 780 .

[0838] As described above, in the organic light emitting display device 700, the OLED D in the red pixel RP, the green pixel GP, and the blue pixel BP emits white light, and the white light from the organic light emitting diode D passes through the red color filter 782, the green color filter 784, and the blue color filter 786. As a result, red light, green light, and blue light are provided from the red pixel RP, the green pixel GP, and the blue pixel BP, respectively.

[0839] exist Figure 7 In the embodiment, the OLED D emitting white light is used for a display device. Alternatively, the OLED D may be formed on the entire surface of the substrate without at least one of a driving element and a color filter layer for a lighting device. A display device and a lighting device each including the OLED D of the present disclosure may be referred to as an organic light emitting device.

[0840] [OLED]

[0841] On the anode (ITO), HIL (compound of Formula 14, ), HTL (compound of formula 15, )、EBL(EML, ), green EML (first host (NH), second host (PH), and dopant (compound GD1 of Formula 13, 7 wt%), ), ETL (compound of formula 16, )、EIL(LiF, ) and cathode (Al, ) to manufacture OLED.

[0842] [Formula 14]

[0843]

[0844] [Formula 15]

[0845]

[0846] [Formula 16]

[0847]

[0848] The green EML is formed by using the first compound of Formula 1c as a first host "NH" and the second compound of Formula 2a as a second host "PH" as a material combination, and the EBL is formed by using the compound of Formula 11 and the compound of Formula 17 as electron blocking materials.

[0849] [Formula 17]

[0850]

[0851] The deuteration rates of the electron blocking material, the first compound "NH" and the second compound "PH" are listed in Table 15.

[0852] Table 15

[0853]

[0854]

[0855] The luminous properties of the OLED, namely, driving voltage (V), luminous efficiency (Efficiency) and lifetime (L), were measured and listed in Table 16.

[0856] Table 16

[0857]

[0858]

[0859]

[0860]

[0861]

[0862]

[0863]

[0864]

[0865]

[0866]

[0867]

[0868]

[0869]

[0870]

[0871]

[0872]

[0873]

[0874]

[0875]

[0876]

[0877]

[0878]

[0879]

[0880]

[0881]

[0882]

[0883]

[0884]

[0885]

[0886]

[0887]

[0888]

[0889] Referring to Table 15, compounds EBL_Ref1, EBL_Ref7 and EBL_Ref9 are non-deuterated compounds, and compounds EBL1-1, EBL1-2, EBL1-3, EBL7-1, EBL7-2, EBL7-3, EBL9-1, EBL9-2 and EBL9-3 are partially deuterated compounds or fully deuterated compounds.

[0890] As shown in Table 16, the lifetime of OLEDs using compounds EBL1-1, EBL1-2, EBL1-3, EBL7-1, EBL7-2, EBL7-3, EBL9-1, EBL9-2 and EBL9-3 is significantly increased compared to OLEDs using compounds EBL_Ref1, EBL_Ref7 and EBL_Ref9 in EBL.

[0891] That is, when the EBL includes the partially or completely deuterated compound of Formula 10, the lifetime of the OLED is significantly increased.

[0892] In addition, the lifetime of the OLED using the compounds EBL1-1, EBL7-1, and EBL9-1 is increased compared to the OLED using the compounds EBL1-2, 7-2, and 9-2. That is, although the deuteration rates of the compounds EBL1-1, EBL7-1, and EBL9-1 are lower than those of the compounds EBL1-2, 7-2, and 9-2, respectively, the lifetime of the OLED using the compounds EBL1-1, EBL7-1, and EBL9-1 is increased because the fluorene moiety or the spirofluorene moiety in the compounds EBL1-1, EBL7-1, and EBL9-1 is deuterated.

[0893] In other words, when the compound of Formula 10 in which the fluorene moiety or the spirofluorene moiety is deuterated is used for the electron blocking layer, the OLED has a sufficient lifespan while minimizing the increase in production cost due to deuterium atoms.

[0894] In addition, the lifespan of OLEDs using compounds 206, 274, 330, 841, 973, and 686 was increased compared to that of OLED using compound 1113.

[0895] That is, when the partially deuterated or fully deuterated first compound "NH" is used, the lifespan of the OLED increases.

[0896] In addition, the lifetime of the OLED using the compound 206 as the first host "NH" is increased compared to the OLED using the compound 973 as the first host "NH". That is, although the deuteration rate of the compound 206 is lower than that of the compound 973, the lifetime of the OLED using the compound 206 is increased because the carbazole part in the compound 206 is deuterated.

[0897] In other words, when the compound of Formula 1 in which the carbazole moiety or the fused carbazole moiety is deuterated is used for the first host of the green EML, the OLED has a sufficient lifespan while minimizing the increase in production cost due to deuterium atoms.

[0898] In addition, when the deuteration rate of the first compound "NH" is greater than the deuteration rate of the second compound "PH", the lifetime of the OLED increases. For example, the lifetime of the OLED using the compound 206 having a deuteration rate of 43% and the compound 2-78 having a deuteration rate of 0% increases compared to the OLED using the compound 1113 having a deuteration rate of 0% and the compound 2-26 having a deuteration rate of 44%.

[0899] It is obvious to those skilled in the art that various modifications and changes can be made to the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Therefore, the present disclosure is intended to cover modifications and changes that fall within the scope of the appended claims and their equivalents.

Claims

1. A heterocyclic compound of formula 1: [Formula 1] Wherein N-Het is represented by Formula 1a or Formula 1b: [Formula 1a] [Formula 1b] In Formula 1a and Formula 1b, R is selected from the group consisting of hydrogen, deuterium, halogen, cyano, deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl, deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl, deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl, deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy, deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl, deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycloalkyl, deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl, and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, wherein L is a direct bond, a deuterated or undeuterated substituted or unsubstituted C6 to C60 arylene group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroarylene group, and a is an integer from 1 to 3, wherein when a is 2 or more, two or more L are the same or different, wherein R1 to R12 are the same or different, wherein each of R1 to R12 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkenyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 alkynyl; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkoxy; deuterated or undeuterated substituted or unsubstituted C3 to C60 cycloalkyl; deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycloalkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; -SiRR'R"; and -NRR', or two or more R1 to R12 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocycle, wherein b is an integer from 1 to 3, wherein when b is 2 or more, two or more R9 are the same or different, wherein R, R' and R" are the same or different, wherein each of R, R' and R" is independently selected from the group consisting of deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; or deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl. 2 . The heterocyclic organic compound according to claim 1 , wherein the deuteration rate of the heterocyclic compound is 20% to 100%.

3. The heterocyclic compound according to claim 1, wherein Formula 1 is divided into the structures of Formula 1-1 to Formula 1-3: [Formula 1-1] [Formula 1-2] [Formula 1-3] wherein N-Het, R1 to R12, L, a and b are the same as those in Formula 1, and the symbol is the bonding position between the structures of Formula 1-1 to Formula 1-3, The deuteration rate of the structure of Formula 1-1, the structure of Formula 1-2 or the structure of Formula 1-3 is 100%, or the deuteration rate of the structure of Formula 1-1, the structure of Formula 1-2 and the structure of Formula 1-3 is 100%.

4. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is one of the compounds of formula 1-4: [Formula 1-4] 5. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is one of the compounds of formula 1-5: [Formula 1-5] 6. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; at least one organic material layer located between the first electrode and the second electrode, wherein one or more of the at least one organic material layer comprises a first compound which is the heterocyclic compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein one or more of the at least one organic material layer further comprises a second compound represented by Formula 2: [Formula 2] wherein Ra and Rb are the same or different, and each of Ra and Rb is independently a deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl group, or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl group, wherein Ra1 to Ra14 are the same or different, and wherein each of Ra1 to Ra14 is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; deuterated or undeuterated substituted or unsubstituted C1 to C60 alkyl; deuterated or undeuterated substituted or unsubstituted C6 to C60 aryl; and deuterated or undeuterated substituted or unsubstituted C2 to C60 heteroaryl, or two or more Ra1 to Ra14 are bonded to each other to form a deuterated or undeuterated substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a deuterated or undeuterated substituted or unsubstituted C2 to C60 heterocyclic ring.

8. The organic light-emitting device according to claim 7, wherein the second compound is one of the compounds of Formula 2b: [Formula 2b] 9 . The organic light-emitting device according to claim 7 , wherein a deuteration rate of the second compound is 20% to 100%.

10. The organic light-emitting device according to claim 7, wherein the at least one organic material layer comprises a first light-emitting material layer and a first electron blocking layer located between the first light-emitting material layer and the first electrode, wherein the first light emitting material layer includes the first compound and the second compound, Wherein the first electron blocking layer includes a first electron blocking material represented by Formula 10: [Formula 10] wherein each of R51 and R52 is independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group, or two R51 and R52 are connected to form a ring, wherein b1 is an integer from 0 to 4, and b2 is an integer from 0 to 5, wherein each of R53 and R54 is independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group, or two R53 and R54 are connected to form a ring, wherein b3 is an integer from 0 to 4, and b4 is an integer from 0 to 5, wherein each of R55 and R56 is hydrogen, or two R55 and R56 are connected to form a ring, and wherein D represents a deuterium atom, each of c1, c2 and c3 represents the number of deuterium atoms, each of c1, c2 and c3 is independently 0 or a positive integer, and at least one of c1, c2 and c3 is a positive integer.

11. The organic light-emitting device according to claim 10, wherein the first electron blocking material is one of the compounds of Formula 11: [Formula 11] 12 . The organic light-emitting device according to claim 10 , wherein c1 is a positive integer, and c2 and c3 are 0.

13. The organic light-emitting device according to claim 12, wherein the first light-emitting material layer further comprises a third compound represented by Formula 12: [Formula 12] wherein each of R61, R62, R63 and R64 is independently selected from the group consisting of substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl, and wherein each of e1, e2, e3 and e4 is independently an integer from 0 to 4, and n is an integer from 1 to 3.

14. The organic light-emitting device according to claim 13, wherein the third compound is one of the compounds of Formula 13: [Formula 13] 15 . The organic light-emitting device according to claim 10 , wherein the at least one organic material layer further comprises a second light-emitting material layer located between the first light-emitting material layer and the second electrode, and a second electron blocking layer located between the first light-emitting material layer and the second light-emitting material layer. 16 . The organic light-emitting device according to claim 6 , wherein the at least one organic material layer comprises a light-emitting material layer, and the light-emitting material layer comprises the first compound. 17 . The organic light-emitting device according to claim 6 , wherein the at least one organic material layer comprises an electron assisting layer, and the electron assisting layer comprises the first compound. 18 . The organic light-emitting device according to claim 6 , wherein the at least one organic material layer comprises a hole blocking layer, and the hole blocking layer comprises the first compound. 19 . The organic light-emitting device of claim 17 , wherein a deuteration rate of the first compound is greater than a deuteration rate of the second compound.

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