Method for producing deuterated anthracene compounds, reaction compositions, deuterated anthracene compounds, and compositions

Abstract

The present specification relates to a method for producing a deuterated anthracene compound, which comprises reacting a halogenated benzene having at least one deuterium with a compound of Chemical Formula 1 to synthesize the deuterated anthracene compound, a reaction composition, a deuterated anthracene compound, and a composition.

Description

[Technical field]

[0001] This specification claims the benefit of the filing date of Korean Patent Application No. 10-2021-0009589, filed with the Korean Intellectual Property Office on January 22, 2021, the entire contents of which are incorporated herein by reference.

[0002] SUMMARY OF THE DISCLOSURE This disclosure relates to methods for making deuterated anthracene compounds, reaction compositions, deuterated anthracene compounds, and compositions. [Background technology]

[0003] Compounds containing deuterium are used for various purposes, such as as labeling compounds for investigating chemical reaction mechanisms or substance metabolism, as well as for medicines, insecticides, organic electroluminescence materials, and other purposes.

[0004] It is known that aromatic compounds are substituted with deuterium to improve the lifespan of organic light-emitting diode (OLED) materials. The principle of this effect is that the LUMO energy of the CD bond becomes lower than that of the CH bond when substituted with deuterium, improving the lifespan of OLED materials.

[0005] In the case of anthracene derivatives used as materials for organic light-emitting devices, HOMO and LUMO are distributed in anthracene. When hydrogen in anthracene is deuterized, the vibrational energy in the molecule of CD bond is reduced compared to CH bond, which reduces the interaction between molecules and improves the life span of organic light-emitting devices.

[0006] The hydrogen-deuterium exchange method is mainly used as a technique for deuterizing aromatic compounds. In the hydrogen-deuterium exchange method, the deuterium source is an organic solvent such as Aceton-d6, DMSO-d6, DMF-d7, MeOH-d4, Toluene-d5, or Benzene-d6, or heavy water (D 2O), using an acid / base catalyst, supercritical heating, using a transition metal catalyst, etc. Such hydrogen-deuterium exchange methods require that the material to be deuterated must be able to withstand reaction conditions such as high temperature and pressure, require multiple treatments to achieve a high level of deuteration, and require a large amount of a relatively expensive deuteration reagent, which can be inefficient in terms of cost and time.

[0007] In order to generalize deuterated aromatic compounds as materials for organic light-emitting devices, a production method that can reduce costs by using less deuterium source is required. Summary of the Invention [Problem to be solved by the invention]

[0008] The present disclosure is directed to methods for making deuterated anthracene compounds, reaction compositions, deuterated anthracene compounds, and compositions. [Means for solving the problem]

[0009] One embodiment of the present specification provides a method for producing a deuterated anthracene compound, comprising the step of reacting a halogenated benzene having at least one deuterium with a compound represented by the following Chemical Formula 1 to synthesize a deuterated anthracene compound: [Chemical formula 1] [ka] In the above Chemical Formula 1, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0010] In addition, another embodiment of the present specification provides a method for producing a deuterated anthracene compound, comprising reacting a halogenated benzene-d5 with a compound of the following formula 1 to synthesize a compound of the following formula 2: [Chemical formula 1] [ka] [Chemical formula 2] [ka] In the above Chemical Formulas 1 and 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and b is an integer from 1 to 8.

[0011] In addition, another embodiment of the present specification provides a reaction composition including a halogenated benzene having at least one deuterium and a compound of the following Chemical Formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0012] Another embodiment of the present specification provides a deuterated anthracene compound produced according to the above-mentioned production method.

[0013] In addition, another embodiment of the present specification provides a composition including an intermediate of the following chemical formula 5. [Chemical formula 5] [ka] In the above Chemical Formula 5, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; a is an integer from 1 to 4. Effect of the Invention

[0014] The manufacturing method of one embodiment herein has the advantage of using less deuterium source, reducing costs.

[0015] The manufacturing methods of other embodiments herein have the advantage of reducing the overall process time for producing deuterated anthracene compounds. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] The present specification will be explained in detail below.

[0017] The hydrogen-deuterium exchange method is mainly used as a technique for deuterizing aromatic compounds. This hydrogen-deuterium exchange method requires that the material to be deuterized must withstand reaction conditions such as high temperature and high pressure, and may require multiple treatments to achieve a high level of deuterium exchange rate, and requires a large amount of a relatively expensive deuterium source, making it inefficient in terms of cost and time.

[0018] This invention relates to a method for synthesizing deuterated anthracene directly from benzene-d6 or halogenated benzene-d5, rather than using a hydrogen-deuterium exchange method, and using the deuterated anthracene as an intermediate for an organic light-emitting material, thereby dramatically reducing the amount of benzene-d6 or halogenated benzene-d5 used.

[0019] In addition, in the case of anthracene derivatives used as materials for organic light-emitting devices, the HOMO and LUMO are distributed in anthracene, so the conversion rate of replacing hydrogen in anthracene with deuterium is important. However, when deuterizing an anthracene derivative in the final state in which a substituent is applied to the 9th, 10th, etc. position of anthracene, it is easy to deuterate the substituent substituted on the anthracene located relatively outside, but it is difficult to replace hydrogen in anthracene that is not substituted with a substituent with deuterium. Therefore, it is no exaggeration to say that the deuterium replacement rate of anthracene derivatives depends on how much hydrogen in anthracene located inside is replaced with deuterium.

[0020] However, since the method for producing a deuterated anthracene compound of the present invention is a bottom-up method in which deuterated anthracene is directly synthesized from benzene-d6 or halogenated benzene-d5, hydrogen atoms at the remaining positions of anthracene except for the 9th and 10th positions are substituted with deuterium atoms before a substituent is substituted at the 9th or 10th position.

[0021] Therefore, in the deuterated anthracene compound produced by the method for producing a deuterated anthracene compound of the present invention, most of the hydrogen atoms of anthracene that are not substituted with a substituent are substituted with deuterium, and an anthracene compound with a high deuterium substitution rate can be more easily produced.

[0022] The present specification provides a method for producing a deuterated anthracene compound, comprising synthesizing the deuterated anthracene compound from benzene-d6 or a halogenated benzene having at least one deuterium.

[0023] The present specification provides a method for producing a deuterated anthracene compound, comprising the step of reacting a halogenated benzene having at least one deuterium with a compound represented by the following Chemical Formula 1 to synthesize a deuterated anthracene compound:

[0024] In one embodiment of the present specification, the halogenated benzene having at least one deuterium may be halogenated benzene-d5.

[0025] In one embodiment of the present specification, the deuterated anthracene compound may be a compound represented by the following formula 2:

[0026] The present specification provides a method for preparing a deuterated anthracene compound, comprising reacting a halogenated benzene-d5 with a compound of the following formula 1 to synthesize a compound of the following formula 2: [Chemical formula 1] [ka] [Chemical formula 2] [ka] In the above Chemical Formulas 1 and 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and b is an integer from 1 to 8.

[0027] In one embodiment of the present specification, b is the number of deuterium atoms, which may be 1 to 8 depending on the number of deuterium atoms substituted.

[0028] In one embodiment herein, b is 1.

[0029] In one embodiment herein, b is 2.

[0030] In one embodiment herein, b is 3.

[0031] In one embodiment herein, b is 4.

[0032] In one embodiment herein, b is 5.

[0033] In one embodiment herein, b is 6.

[0034] In one embodiment herein, b is 7.

[0035] In one embodiment of the present specification, b is 8. When b is 8, the above formula 2 may be the following formula 2-1. [Chemical formula 2-1] [ka] In the above Chemical Formula 2-1, Ar1 and Ar2 are as defined in the above Chemical Formula 2.

[0036] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0037] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0038] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0039] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted thioxanthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzocarbazolyl group, or a substituted or unsubstituted dibenzocarbazolyl group.

[0040] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0041] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0042] In one embodiment of the present specification, Ar1 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0043] In one embodiment of the present specification, Ar2 in Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0044] In one embodiment of the present specification, Ar2 in Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0045] In one embodiment of the present specification, Ar2 in Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0046] In one embodiment of the present specification, Ar2 in the above Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted thioxanthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzocarbazolyl group, or a substituted or unsubstituted dibenzocarbazolyl group.

[0047] In one embodiment of the present specification, Ar2 in Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0048] In one embodiment of the present specification, Ar2 in Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0049] In one embodiment of the present specification, Ar2 in the above-mentioned Chemical Formula 1 or 2 is deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0050] In one embodiment of the present specification, Ar2 in Formula 1 is hydrogen or deuterium.

[0051] In one embodiment of the present specification, Ar2 in Formula 2 is hydrogen or deuterium.

[0052] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 may be any one of the following Chemical Formulas 1-1 to 1-3. [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] In the above Chemical Formulas 1-1 to 1-3, Y is CRaRb, NRc, O or S; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ra, Rb, Rc, and R1 to R3 are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; r1 and r2 are each an integer of 1 to 7, and r3 is an integer of 1 to 5; When r1 is 2 or more, R1 are the same or different, When r2 is 2 or more, R2 are the same or different, When r3 is 2 or more, R3's are the same or different from each other.

[0053] In one embodiment of the present specification, said Y is CRaRb.

[0054] In one embodiment of the present specification, Y is NRc.

[0055] In one embodiment of the present specification, Y is O.

[0056] In one embodiment of the present specification, Y is S.

[0057] In one embodiment of the present specification, Ra and Rb are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0058] In one embodiment of the present specification, Ra and Rb are the same or different and each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0059] In one embodiment of the present specification, Ra and Rb are the same or different and each independently a substituted or unsubstituted aryl group.

[0060] In one embodiment of the present specification, Ra and Rb are the same or different and each independently a substituted or unsubstituted phenyl group.

[0061] In one embodiment of the present specification, Ra and Rb are phenyl groups.

[0062] In one embodiment of the present specification, Rc is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0063] In one embodiment of the present specification, Rc is hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0064] In one embodiment of the present specification, Rc is a substituted or unsubstituted aryl group.

[0065] In one embodiment of the present specification, Rc is a substituted or unsubstituted phenyl group.

[0066] In one embodiment of the present specification, Rc is a phenyl group.

[0067] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon on an aliphatic ring may be interpreted as "adjacent" groups to each other. In addition, substituents connected to two adjacent carbons on an aliphatic ring (a total of four) may also be interpreted as "adjacent" groups.

[0068] As used herein, the expression "adjacent groups are bonded to each other to form a ring" among substituents means that adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0069] As used herein, the term "a 5- or 6-membered ring formed by bonding adjacent groups" means that the ring including the substituents participating in the formation of the ring is 5- or 6-membered. It may include the condensation of an additional ring to the ring including the substituents participating in the formation of the ring.

[0070] In this specification, an aromatic hydrocarbon ring refers to a hydrocarbon ring in which pi electrons are completely conjugated to form a planar ring, and the explanation for the aryl group described below is applicable, except that the ring is divalent.

[0071] In this specification, the term "aliphatic hydrocarbon ring" refers to a ring that is a ring bonded to a ring and is not aromatic. Examples of the aliphatic hydrocarbon ring include cycloalkyl and cycloalkane, and the description of the cycloalkyl group described below can be applied to cycloalkyl except that it is divalent, and cycloalkane means that one or more of the single bonds in the cycloalkyl are replaced with double bonds. In addition, the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.

[0072] In this specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring form a condensed ring. Examples of the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring include, but are not limited to, a 1,2,3,4-tetrahydronaphthalene group and a 2,3-dihydro-1H-indene group.

[0073] In this specification, the description of the heterocyclic group described below can be applied, except that the heterocyclic ring is divalent.

[0074] In one embodiment of the present specification, Ra, Rb, Rc and R1 to R3 may each independently bond to adjacent groups to form a substituted or unsubstituted ring.

[0075] In one embodiment of the present specification, Ra, Rb, Rc, and R1 to R3 may each independently bond to adjacent groups to form a direct bond; a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0076] In one embodiment of the present specification, Ra, Rb, Rc, and R1 to R3 may each independently bond to adjacent groups to form a direct bond; a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0077] In one embodiment of the present specification, Ra, Rb, Rc, and R1 to R3 may each independently bond to adjacent groups to form a direct bond; a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted indene ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring.

[0078] In one embodiment of the present specification, Ra, Rb, Rc and R1 to R3 each independently bond to adjacent groups to form a direct bond; or may form a substituted or unsubstituted benzene ring.

[0079] In one embodiment of the present specification, Ra, Rb, Rc and R1 to R3 may each independently bond to adjacent groups to form a substituted or unsubstituted benzene ring.

[0080] In one embodiment of the present specification, each R1 may independently bond to adjacent groups to form a substituted or unsubstituted benzene ring.

[0081] In one embodiment of the present specification, each R2 may independently bond to adjacent groups to form a substituted or unsubstituted benzene ring.

[0082] In one embodiment of the present specification, each R3 may independently bond to adjacent groups to form a substituted or unsubstituted benzene ring.

[0083] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 has any of the following structures. [ka] [ka] [ka] .

[0084] In one embodiment of the present specification, the step of synthesizing the compound of Chemical Formula 2 may be performed by synthesizing the compound of Chemical Formula 2 using a solution containing halogenated benzene-d5, the compound of Chemical Formula 1, 2,2,6,6-Tetramethylpiperidine, alkyl lithium, and an ether solvent.

[0085] In one embodiment of the present invention, the alkyllithium may be, for example, butyllithium.

[0086] In one embodiment of the present specification, the ether solvent may be, for example, tetrahydropyran.

[0087] In one embodiment of the present specification, the chemical formula 2 has any one of the following structures: [ka] [ka] [ka] [ka] [ka] .

[0088] Here, b is the number of deuterium substitutions, and is an integer of 1 to 8. b is determined by the deuterium conversion rate of deuterium substituted by the synthesis method and conditions, the number of deuterium substituted in each compound, and the substitution position of deuterium substituted in each compound. Even if compounds having the same backbone are produced, there may be compounds with different numbers and substitution positions of deuterium among the individual compounds.

[0089] In one embodiment of the present specification, a method for producing a deuterated anthracene compound may include synthesizing a compound represented by the following Chemical Formula 3 using a compound represented by the above Chemical Formula 2, in which Ar2 is hydrogen, and a solution containing a halogen donor.

[0090] In one embodiment of the present specification, a method for producing a deuterated anthracene compound may include a step of synthesizing a compound of the following Chemical Formula 3 using a compound of the above Chemical Formula 2, in which Ar2 is hydrogen, and a solution containing a halogen donor; and a step of reacting the above Chemical Formula 3 with L-Ar2 to synthesize a compound of the following Chemical Formula 4. [Chemical formula 3] [ka] [Chemical formula 4] [ka] Here, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; X represents a halogen group; L represents a leaving group; and b represents an integer of 1 to 8.

[0091] In the above Chemical Formula 3, b is the number of deuterium atoms, which may be 1 to 8 depending on the number of deuterium atoms substituted.

[0092] In the above Chemical Formula 3, b is 1.

[0093] In the above Chemical Formula 3, b is 2.

[0094] In the above Chemical Formula 3, b is 3.

[0095] In the above Chemical Formula 3, b is 4.

[0096] In the above Chemical Formula 3, b is 5.

[0097] In the above formula 3, b is 6.

[0098] In the above Chemical Formula 3, b is 7.

[0099] In the above Chemical Formula 3, b is 8. When b is 8, the above Chemical Formula 3 may be the following Chemical Formula 3-1. [Chemical formula 3-1] [ka] In the formula 3-1, Ar1 and X are as defined in the formula 3.

[0100] In the above Chemical Formula 4, b is the number of deuterium atoms, which may be 1 to 8 depending on the number of deuterium atoms substituted.

[0101] In the above Chemical Formula 4, b is 1.

[0102] In the above Chemical Formula 4, b is 2.

[0103] In the above Chemical Formula 4, b is 3.

[0104] In the above Chemical Formula 4, b is 4.

[0105] In the above Chemical Formula 4, b is 5.

[0106] In the above Chemical Formula 4, b is 6.

[0107] In the above Chemical Formula 4, b is 7.

[0108] In the above Chemical Formula 4, b is 8. When b is 8, the above Chemical Formula 4 may be the following Chemical Formula 4-1. [Chemical formula 4-1] [ka] In the above Chemical Formula 4-1, Ar1 and Ar2 are as defined in the above Chemical Formula 4.

[0109] In one embodiment herein, X is fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

[0110] In one embodiment herein, X is chlorine (-Cl), bromine (-Br) or iodine (-I).

[0111] In one embodiment herein, X is bromine (-Br).

[0112] In one embodiment of the present specification, Ar2 in Chemical Formula 4 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0113] In one embodiment of the present specification, Ar2 in Chemical Formula 4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0114] In one embodiment of the present specification, Ar2 in Chemical Formula 4 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0115] In one embodiment of the present specification, Ar2 in Chemical Formula 4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted thioxanthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzocarbazolyl group, or a substituted or unsubstituted dibenzocarbazolyl group.

[0116] In one embodiment of the present specification, Ar2 in Chemical Formula 4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0117] In one embodiment of the present specification, Ar2 in Formula 4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0118] In one embodiment of the present specification, Ar2 in Formula 4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0119] In one embodiment of the present specification, Ar2 in Formula 4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0120] In one embodiment herein, L is -B(OH). 2 It is.

[0121] In one embodiment herein, L-Ar2 is any of the following structures: [ka] [ka] [ka] .

[0122] In one embodiment of the present specification, the formula 3 has any of the following structures: [ka] [ka] [ka] [ka] [ka] .

[0123] Here, b is the number of deuterium substitutions, and is an integer of 1 to 8. b is determined by the deuterium conversion rate of deuterium substituted by the synthesis method and conditions, the number of deuterium substituted in each compound, and the substitution position of deuterium substituted in each compound. Even if compounds having the same backbone are produced, there may be compounds with different numbers and substitution positions of deuterium among the individual compounds.

[0124] In one embodiment of the present specification, the formula 4 has any one of the following structures: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0125] Here, b is the number of deuterium substitutions, and is an integer of 1 to 8. b is determined by the deuterium conversion rate of deuterium substituted by the synthesis method and conditions, the number of deuterium substituted in each compound, and the substitution position of deuterium substituted in each compound. Even if compounds having the same backbone are produced, there may be compounds with different numbers and substitution positions of deuterium among the individual compounds.

[0126] In one embodiment of the present specification, the halogen donor for synthesizing the compound of Chemical Formula 3 is not particularly limited as long as it can provide a halogen to the 10-position of the compound of Chemical Formula 2. For example, it may be selected from the group consisting of N-bromosuccinimide, bromine, and hydrogen bromide.

[0127] In one embodiment of the present specification, the method for producing a deuterated anthracene compound may further include a step of synthesizing benzene-d6 into halogenated benzene-d5 using a halogen donor before the step of synthesizing the compound of Chemical Formula 2.

[0128] In one embodiment of the present specification, the halogen donor for synthesizing halogenated benzene-d5 is not particularly limited as long as it can replace one deuterium in benzene-d6 with a halogen. For example, KBrO 3 , Bromine and hydrogen bromide.

[0129] The present specification provides a reaction composition including a halogenated benzene having at least one deuterium and the compound of Chemical Formula 1.

[0130] The reaction composition can be described in the above-mentioned method for producing a deuterated anthracene compound.

[0131] The present specification provides a deuterated anthracene compound produced by the above-mentioned production method.

[0132] In one embodiment of the present specification, the deuterated anthracene compound may include a compound represented by the following chemical formula A: [Chemical formula A] [ka] In the above chemical formula A, L21 to L23 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; R21 to R27 are the same or different and each independently represent a hydrogen atom; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar21 to Ar23 are the same or different and each independently represents deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; a is 0 or 1.

[0133] The present specification provides a deuterated anthracene compound represented by the following formula 2: [Chemical formula 2] [ka] In the above Chemical Formula 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and b is an integer from 1 to 8.

[0134] The present specification provides an intermediate of the following formula 5: [Chemical formula 5] [ka] In the above Chemical Formula 5, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; a is an integer from 1 to 4.

[0135] The present specification provides a composition including an intermediate of the following formula 5: [Chemical formula 5] [ka] In the above Chemical Formula 5, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; a is an integer from 1 to 4.

[0136] In the above Chemical Formula 5, a is the number of deuterium atoms, which may be 1 to 8 depending on the number of deuterium atoms substituted.

[0137] In the above Chemical Formula 5, a is 1.

[0138] In the above Chemical Formula 5, a is 2.

[0139] In the above Chemical Formula 5, a is 3.

[0140] In the above Chemical Formula 5, a is 4. When a is 4, the above Chemical Formula 5 may be the following Chemical Formula 5-1. [Chemical formula 5-1] [ka] In the above Chemical Formula 5-1, Ar1 and Ar2 are as defined in the above Chemical Formula 5.

[0141] In one embodiment of the present specification, the composition may further include a compound of the following Chemical Formula 2: [Chemical formula 2] [ka] In the above Chemical Formula 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and b is an integer from 1 to 8.

[0142] In one embodiment of the present specification, the composition containing the intermediate of Chemical Formula 5 may be a solution in a step of synthesizing a deuterated anthracene compound by reacting a halogenated benzene having at least one deuterium with a compound of Chemical Formula 1 below.

[0143] In one embodiment of the present specification, the intermediate of Chemical Formula 5 is an intermediate formed by reacting a halogenated benzene having at least one deuterium with a compound of Chemical Formula 1 in a 1:1 ratio, and during the reaction to synthesize the deuterated anthracene compound, which is the product, the intermediate of Chemical Formula 5 is generated several times and then disappears while forming the deuterated anthracene compound. In addition, even after the synthesis of the deuterated anthracene compound is completed, an intermediate that has not completely become the deuterated anthracene compound may remain.

[0144] In one embodiment of the present specification, even after the deuterated anthracene compound is purified, the intermediate of Formula 5 may remain as an impurity. Therefore, the composition containing the intermediate of Chemical Formula 5 may refer to a solution during the synthesis reaction according to the preparation method of the present disclosure, a solution after the synthesis reaction according to the preparation method of the present disclosure has been completed, or a deuterated anthracene compound obtained after the synthesis reaction according to the preparation method of the present disclosure has been completed.

[0145] In this case, the deuterated anthracene compound obtained after the synthesis reaction can contain two or more isotopes with different molecular weights depending on the number of deuterium substituted, and therefore can be expressed as a composition containing two or more compounds with different numbers of deuterium substitutions.

[0146] In one embodiment of the present specification, even if the hydrogen of the substituents of Ar1 and Ar2 is not replaced with deuterium, the deuterated anthracene compound obtained after the synthesis reaction is completed exhibits a similar life improvement effect to an anthracene compound having a deuterium substitution rate of a certain level or more (80% or more) without performing an additional deuterium substitution reaction, since the HOMO and LUMO of the anthracene derivative are distributed in anthracene.

[0147] Since an additional deuteration substitution reaction is not required, an excess amount of deuterium source is not required for the deuteration substitution reaction, which is advantageous in terms of cost and enables the production of a deuterated anthracene compound at low cost.

[0148] In one embodiment of the present specification, in the deuterated anthracene compound of the present specification, most of the positions among the 1-10 positions of anthracene that are not "substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocycles" are substituted with deuterium.

[0149] In one embodiment of the present specification, the deuterated anthracene compound of the present specification may have a deuterium substitution rate at positions 1 to 10 of anthracene that are not "substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocycles" of 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, 95% or more, 96% or more, 97% or more, 98% or more, or 99% or more.

[0150] In one embodiment of the present specification, when a deuterated anthracene compound is substituted with a "substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle" only at the 9- and 10-positions, the number of deuterium substitutions of the deuterated anthracene compound may be 5 or more, 6 or more, 7 or more, or 8.

[0151] In one embodiment of the present specification, in the case of a deuterated anthracene compound having a "substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle" substituted only at the 9-position, the number of deuterium substitutions of the deuterated anthracene compound may be 5 or more, 6 or more, 7 or more, 8 or more, or 9.

[0152] In one embodiment of the present specification, when a deuterated anthracene compound is substituted with "substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocycles" only at the 2-, 9-, and 10-positions, the number of deuteration substitutions of the deuterated anthracene compound may be 5 or more, 6 or more, or 7.

[0153] In one embodiment of the present specification, when the deuterated anthracene compound has no positions substituted with a “substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle” at positions 1 to 10, the number of deuterium substitutions in the deuterated anthracene compound may be 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10.

[0154] Examples of the substituents are described below in this specification, but are not limited thereto.

[0155] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0156] In the present specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, amine, silyl, boron, alkoxy, alkyl, cycloalkyl, aryl, and heterocyclic groups, or that the group is substituted with a substituent in which two or more of the above-listed substituents are linked, or that the group does not have any substituents. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are linked.

[0157] As used herein, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

[0158] As used herein, a silyl group is -SiY a Y b Y c wherein Y is a cyclic alkyl group; a , Y b and Y c may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0159] As used herein, the boron group is represented by -BY d Y e wherein Y is a cyclic alkyl group; d and Y e may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a tert-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0160] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to still another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, and an n-octyl group.

[0161] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 20. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc.

[0162] The alkyl groups, alkoxy groups and other alkyl moiety-containing substituents described herein include either straight or branched chain configurations.

[0163] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to still another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0164] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 39 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a ferrylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc.

[0165] As used herein, the fluorene group may be substituted, and two substituents may be bonded together to form a spiro structure.

[0166] When the fluorene group is substituted, [ka] However, the present invention is not limited to this.

[0167] In the present specification, the heterocyclic group is a ring group containing at least one of heteroatoms N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 36. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, an indenocarbazole group, and an indolocarbazole group.

[0168] In this specification, the above explanation regarding the heterocyclic group can be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0169] As used herein, an amine group is defined as -NH 2 It can be selected from the group consisting of: alkylamine groups; N-alkylarylamine groups; arylamine groups; N-arylheteroarylamine groups; N-alkylheteroarylamine groups, and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group.

[0170] As used herein, an N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.

[0171] As used herein, an N-arylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group. As used herein, an N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group. In this specification, the alkylamine group, the N-alkylarylamine group, the arylamine group, the N-arylheteroarylamine group, the N-alkylheteroarylamine group and the alkyl group, the aryl group and the heteroaryl group in the heteroarylamine group are the same as the above-mentioned exemplified alkyl group, aryl group and heterocyclic group, respectively.

[0172] In one embodiment of the present specification, the deuterated anthracene compound may have any of the following structures: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] Here, b is an integer from 1 to 8.

[0173] Theoretically, if all hydrogen in a deuterated compound is replaced with deuterium, i.e., the deuterium replacement rate is 100%, the life characteristics will be most ideally improved. However, there are problems such as extreme conditions being required due to steric hindrance, or the compound being destroyed by a side reaction before being deuterized, so in reality it is difficult to obtain a 100% deuterium replacement rate for all hydrogen in a compound. Even if a deuterium replacement rate approaching 100% can be obtained, the investment efficiency is not good when considering process time, cost, etc.

[0174] In this specification, a deuterated compound having one or more deuterium atoms produced by a deuteration reaction is produced as a composition having two or more isotopes whose molecular weights differ depending on the number of substituted deuterium atoms, so the position where deuterium is substituted in the structure is omitted.

[0175] In the compound of the above structure, at least one of the positions where hydrogen is omitted and which is represented or substituted by hydrogen may be substituted by deuterium.

[0176] The present specification provides an electronic device including a deuterated anthracene compound produced by the above-mentioned production method.

[0177] The present specification provides an electronic device including the above-mentioned deuterated anthracene compound.

[0178] The present specification provides a method for producing an electronic device, comprising the step of producing an electronic device using the deuterated anthracene compound described above.

[0179] The electronic device and the method for manufacturing the electronic device may refer to the applicable descriptions among those described above, and redundant descriptions will be omitted.

[0180] The electronic device is not particularly limited as long as it is an element in which the above-mentioned deuterated anthracene compound can be used, and may be, for example, an organic light-emitting device, an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, or the like.

[0181] The electronic device includes a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, and at least one of the organic layers may include the deuterated anthracene compound described above.

[0182] The present specification provides an organic light-emitting device including the deuterated anthracene compound described above.

[0183] The present specification provides an organic light-emitting device including a deuterated anthracene compound produced by the above-mentioned production method.

[0184] In one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, and the organic layer includes the deuterated anthracene compound.

[0185] In one embodiment of the present specification, the organic layer includes a light-emitting layer containing the deuterated anthracene compound.

[0186] The organic layer of the organic light-emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic layer of the present specification may be composed of one to three layers. In addition, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0187] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0188] For example, the organic light emitting device of the present invention may be fabricated by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and a material that can be used as a cathode may be deposited thereon. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0189] In addition, the material of each layer can be formed as an organic layer by a solution coating method as well as a vacuum deposition method during the manufacture of the organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0190] In one embodiment herein, the first electrode is an anode and the second electrode is a cathode.

[0191] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0192] In another embodiment, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

[0193] In another embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate.

[0194] In the present specification, the materials of the cathode, the organic layer, and the anode are not particularly limited except that at least one of the organic layers contains a deuterated anthracene compound, and materials known in the art may be used.

[0195] In the present specification, the above-mentioned deuterated anthracene compound may be used in electronic devices such as organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors, etc., based on the same principle as that applied to organic light-emitting devices. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the selected deuterated anthracene compound. EXAMPLES

[0196] The present invention will be described in more detail below through examples. However, the following examples are intended to illustrate the present invention, and are not intended to limit the present invention. In all of the examples, (D) b , (D) c , (D) d (D) e (D) f and (D) g Each of b to g means the number of deuterium substitutions, and since the number and position of deuterium substitutions of individual compounds among the obtained compounds may differ depending on the deuterium conversion rate of each reaction, the number of deuterium substitutions b to g and the substitution position are not specified, where b is an integer of 1 to 8, c is an integer of 1 to 6, d is an integer of 1 to 5, e is an integer of 1 to 4, f is an integer of 1 to 7, and g is an integer of 1 to 7.

[0197] [Measurement of deuterium conversion rate and anthracene deuterium conversion rate] In this specification, the deuterium conversion rate and the anthracene deuterium conversion rate were measured by nuclear magnetic resonance (NMR) analysis. The detailed NMR analysis method is as follows.

[0198] After N-NMR analysis of a compound not substituted with deuterium, a material with the same structure as the compound analyzed by N-NMR but with hydrogen substituted with deuterium and an internal standard were mixed and analyzed by H-NMR. If hydrogen is 100% substituted with deuterium, hydrogen peaks at the positions substituted with deuterium cannot be observed in H-NMR, so the deuterium substitution rate for each position can be measured based on the H-NMR analysis results of the product not substituted with deuterium and the H-NMR analysis results of the deuterium substituted material.

[0199] However, in Production Examples 1 to 12 described later, the hydrogen position of anthracene in H-NMR may overlap with the hydrogen position of the substituent depending on the substituent. In this specification, when a substituent is introduced into 9-Bromo-10-(1-naphthyl)anthracene-d8, the substitution rate of anthracene deuterium is replaced with the substitution rate of deuterium of 9-Bromo-10-(1-naphthyl)anthracene-d8.

[0200] [Production Example 1] Synthesis of Bromobenzene-d5 [ka] Benzene-d6 [Benzene-d6, deuterium conversion rate 99%] (100 g, 1.18 mol) was dissolved in 30 wt% H 2 SO 4 (240 ml, 7.34 mol) was added and stirred at 40°C. 3 After adding five portions, the reaction was monitored using high performance liquid chromatography (HPLC). After the reaction was completed, the layers were separated to obtain 1-bromobenzene-2,3,4,5,6-d5 (140 g, 73%, deuterium conversion rate 99%).

[0201] [Production example 2] 9-Aryl substituted anthracene synthesis

[0202] A. Synthesis of 9-(naphthalen-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 [ka] Under nitrogen, 2,2,6,6-Tetramethylpiperidine (TMP) (26.2 g, 0.185 mol) was added to anhydrous tetrahydropyran (THP) (100 mL) and stirred at 0°C. While maintaining the temperature, 1-(naphthalen-1-yl)ethan-1-one (10.52 g, 0.062 mol), 2.5 M n-BuLi (98.7 mL, 0.247 mol) and Bromobenzene-d5 (20 g, 0.123 mol) were added in that order, and the temperature was raised to reflux. After 30 minutes, the mixture was cooled and quenched by adding 100 mL of water, and the aqueous layer was removed using a separatory funnel. The organic layer was then washed with MgSO 4 The water was removed by filtration through a silica pad. The filtrate was purified by column chromatography to give 9-(naphthalen-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 (7.8 g, 0.025 mol, yield 40%, deuterium conversion rate of anthracene 99%).

[0203] Synthesis of 9-(naphthalen-2-yl)anthracene-1,2,3,4,5,6,7,8-d8 [ka] Under nitrogen, 2,2,6,6-Tetramethylpiperidine (26.2g, 0.185mol) was added to anhydrous tetrahydropyran (100mL) and stirred at 0°C. While maintaining the temperature, 1-(naphthalen-2-yl)ethan-1-one (10.52g, 0.062mol), 2.5M n-BuLi (98.7mL, 0.247mol), and bromobenzene-d5 (20g, 0.123mol) were added in that order, and the temperature was raised to reflux. After 30 minutes, the mixture was cooled and quenched by adding 100mL of water, and the aqueous layer was removed using a separatory funnel. The organic layer was then washed with MgSO 4The water was removed by filtration through a silica pad. The filtrate was purified by column chromatography to obtain 9-(naphthalen-2-yl)anthracene-1,2,3,4,5,6,7,8-d8 (7.8 g, 0.025 mol, yield 40%, deuterium conversion rate of anthracene 99%).

[0204] C. Synthesis of 2-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan [ka] Under nitrogen, 2,2,6,6-Tetramethylpiperidine (26.2 g, 0.185 mol) was added to anhydrous tetrahydropyran (100 mL) and stirred at 0°C. While maintaining the temperature, 1-(dibenzo[b,d]furan-2-yl)ethan-1-one (13.02 g, 0.062 mol), 2.5M n-BuLi (98.7 mL, 0.247 mol), and Bromobenzene-d5 (20 g, 0.123 mol) were added in that order, and the temperature was raised to reflux. After 30 minutes, the mixture was cooled, quenched by adding 100 mL of water, and the aqueous layer was removed using a separatory funnel. The organic layer was then washed with MgSO 4 The water was removed by filtration through a silica pad, and the filtrate was purified by column chromatography to obtain 2-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan (8.09 g, 0.023 mol, yield 37%, deuterium conversion rate of anthracene 99%).

[0205] 2. Synthesis of 4-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan [ka] Under nitrogen, 2,2,6,6-Tetramethylpiperidine (26.2g, 0.185mol) was added to anhydrous tetrahydropyran (100mL) and stirred at 0°C. While maintaining the temperature, 1-(dibenzo[b,d]furan-4-yl)ethan-1-one (10.52g, 0.062mol), 2.5M n-BuLi (98.7mL, 0.247mol) and Bromobenzene-d5 (20g, 0.123mol) were added in that order, and the temperature was raised to reflux. After 30 minutes, the mixture was cooled, quenched by adding 100mL of water, and the aqueous layer was removed using a separatory funnel. The organic layer was then washed with MgSO 4 The water was removed by filtration through a silica pad, and the filtrate was purified by column chromatography to obtain 4-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan (8.09 g, 0.023 mol, yield 37%, deuterium conversion rate of anthracene 99%).

[0206] E. Synthesis of 1-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)-9-phenyl-9H-carbazole [ka] Under nitrogen, 2,2,6,6-Tetramethylpiperidine (26.2 g, 0.185 mol) was added to anhydrous tetrahydropyran (100 mL) and stirred at 0°C. While maintaining the temperature, 1-(9-phenyl-9H-carbazol-1-yl)ethan-1-one (17.67 g, 0.062 mol), 2.5 M n-BuLi (98.7 mL, 0.247 mol) and Bromobenzene-d5 (20 g, 0.123 mol) were added in that order, and the temperature was raised to reflux. After 30 minutes, the mixture was cooled and quenched by adding 100 mL of water, and the aqueous layer was removed using a separatory funnel. The organic layer was then washed with MgSO 4The water was removed by filtration through a silica pad, and the filtrate was purified by column chromatography to obtain 1-(anthracen-9-yl-1,2,3,4,5,6,7,8-d8)-9-phenyl-9H-carbazole (9.8 g, 0.023 mol, yield 37%, deuterium conversion rate of anthracene 99%).

[0207] [Production Example 3] 9-Aryl-10-Bromoanthracene synthesis A. Synthesis of 9-Bromo-10-(1-naphthyl)anthracene-d8 [ka] While stirring 9-(1-Naphthyl)anthracene (5 g, 0.016 mol) and N,N-dimethylformamide (DMF) (30 mL), N-bromosuccinimide (NBS) (2.8 g, 0.016 mol) was added. After 5 hours, water (100 mL) was added and the resulting crystals were filtered. The filtered solid was dissolved in Chloroform (50 mL), washed with water (15 mL), and then dissolved in MgSO 4 The filtrate was distilled under reduced pressure and purified by column chromatography to obtain 9-Bromo-10-(1-naphthyl)anthracene (5.64 g, yield 90%, deuterium conversion rate of anthracene 99%, m / s(M+H) 320).

[0208] [Production Example 4] Synthesis of BH1 [ka] In a round-bottom flask, add 9-Bromo-10-(1-naphthyl)anthracene-d8 (10 g, 0.026 mol), (4-(naphthalen-2-yl)phenyl)boronic acid (7.6 g, 0.031 mol), 1,4-Dioxane (200 mL), potassium phosphate (10.8 g, 0.052 mol), and H 2After adding 2H2O (32.4 mL) and Bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.13 g, 0.0026 mol), the mixture was heated to reflux. After 5 hours, the reaction mixture was cooled and the aqueous layer was removed using a separatory funnel. The organic layer was separated using MgSO 4 After drying at 40° C., the mixture was filtered through a silica pad. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain BH1 (8.5 g, yield 65%, deuterium conversion rate of anthracene 99%, m / s(M+H) 515).

[0209] [Production Example 5] Synthesis of BH2 [ka] BH2 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 5. (Yield: 8.1 g, yield: 73%, deuterium conversion rate of anthracene: 99%, m / s(M+H) 439)

[0210] [Production Example 6] Synthesis of BH3 [ka] BH3 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 6. (Yield 9.3 g, yield 70%, deuterium conversion rate of anthracene 99%, m / s(M+H) 479)

[0211] [Production Example 7] Synthesis of BH4 [ka] BH4 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 7. (Yield 9.1 g, yield 75%, deuterium conversion rate of anthracene 99%, m / s(M+H) 479)

[0212] [Production Example 8] Synthesis of BH5 [ka] BH5 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 8. (Yield: 8.7 g, yield: 65%, deuterium conversion rate of anthracene: 99%, m / s(M+H) 529)

[0213] [Production Example 9] Synthesis of BH6 [ka] BH6 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 9. (Yield 9.4 g, yield 70%, deuterium conversion rate of anthracene 99%, m / s(M+H) 529)

[0214] [Production Example 10] Synthesis of BH7 [ka] BH7 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 10. (Yield: 11.5 g, yield: 80%, deuterium conversion rate of anthracene: 99%, m / s(M+H) 569)

[0215] [Production Example 11] Synthesis of BH8 [ka] BH8 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 11. (Yield: 10.1 g, yield: 70%, deuterium conversion rate of anthracene: 99%, m / s(M+H) 569)

[0216] [Production Example 12] Synthesis of BH9 [ka] BH9 was synthesized in the same manner as in Preparation Example 4, except that reactants with different structures were used in Preparation Example 12. (Yield 8.9 g, yield 65%, deuterium conversion rate of anthracene 99%, m / s(M+H) 534)

[0217] [Comparative Synthesis Example 1] Synthesis of BH10 [ka] In a round-bottom flask, add 9-Bromo-10-(1-naphthyl)anthracene (10 g, 0.026 mol), (4-(naphthalen-2-yl)phenyl)boronic acid (7.6 g, 0.031 mol), 1,4-Dioxane (200 mL), potassium phosphate (10.8 g, 0.052 mol), and H 2 After adding 2H2O (32.4 mL) and Bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.0026 mol), the mixture was heated to reflux. After 5 hours, the reaction mixture was cooled and the aqueous layer was removed using a separatory funnel. The organic layer was separated using MgSO 4 The mixture was dried at 40° C. and then filtered through a silica pad. The filtrate was distilled under reduced pressure and purified by column chromatography to give BH10 (10.2 g, yield 65%, m / s (M+H) 506).

[0218] [Comparative Synthesis Example 2] Synthesis of BH11 [ka] BH11 was synthesized in the same manner as in Comparative Synthesis Example 1, except that a reactant having a different structure was used in Comparative Synthesis Example 2. (Yield: 8.4 g, yield: 75%, m / s (M+H) 430)

[0219] [Comparative Synthesis Example 3] Synthesis of BH12 [ka] BH10 (10 g, 0.020 mol), Benzene-d6 (475 g, 5.65 mol) and trifluoromethanesulfonic acid (TfOH) (13.5 g, 0.09 mol) were added to a round-bottom flask and then heated to 70°C. After 2 hours, the reaction solution was cooled and then added to 2M K 3 PO 4 After neutralizing with 150 ml of (aq), the aqueous layer was removed using a separatory funnel. The organic layer was separated using MgSO 4After drying at 400°C, it was filtered through a silica pad. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain BH12 (9.4 g, yield 90%, deuterium conversion rate 87%, anthracene deuterium conversion rate 91%). Here, the molecular weight of BH12 was confirmed by distribution. [cal.m / s: 532, exp.m / s (M+H) 524~533]

[0220] [Comparative Synthesis Example 4] Synthesis of BH13 [ka] BH13 was synthesized in the same manner as in Comparative Synthesis Example 3, except that BH11 was used instead of BH10 in Comparative Synthesis Example 3. (Yield 8.1 g, yield 78%, deuterium conversion rate 85%, anthracene deuterium conversion rate 87.5%). Here, the molecular weight distribution of BH13 was confirmed. [cal.m / s: 452, exp.m / s (M+H) 443~452]

[0221] [Evaluation example] Fabrication of OLED elements A glass substrate coated with a 150 nm-thick thin film of ITO (indium tin oxide) was placed in distilled water containing detergent and ultrasonically washed. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered twice with a filter made by Millipore Co. The ITO was washed for 30 minutes, and then ultrasonically washed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and the substrate was dried and then transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using nitrogen plasma, and then transferred to a vacuum evaporator. The following HAT-CN compound was thermally vacuum deposited on the ITO transparent electrode to a thickness of 5 nm to form a hole injection layer. Then, HT1 was thermally vacuum deposited to a thickness of 100 nm, and then HT2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Next, any one of the following BH1 to BH11 as a host and BD as a dopant (weight ratio 97:3) were simultaneously vacuum-deposited to form a 20 nm-thick light-emitting layer. Then, ET was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Next, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Next, aluminum was vapor-deposited to a thickness of 100 nm to form a cathode, and an organic light-emitting device was produced.

[0222] The structures of the compounds used in the examples are as follows: [ka] [ka] [ka]

[0223] In the organic light-emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 4, 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm. 2The time (LT) required for the luminance to reach 95% of the initial luminance was measured at the current density of 100 mA. The results are shown in Table 1 below.

[0224] [Table 1]

[0225] According to Table 1, it can be seen that Examples 1 to 9, which use compounds substituted with deuterium, have lower driving voltages, higher luminous efficiencies, or longer lifetimes than Comparative Examples 1 and 2, which use compounds not substituted with deuterium.

[0226] In particular, when Example 1 using BH1 with the same backbone structure is compared with Comparative Example 1 using BH10, it can be seen that the lifetime of Example 1 in which deuterium is substituted is significantly longer than that of Comparative Example 1. In addition, when Example 2 using BH2 with the same backbone structure is compared with Comparative Example 2 using BH11, it can be seen that the lifetime of Example 2 in which deuterium is substituted is significantly longer than that of Comparative Example 2.

[0227] BH1 used in Example 1 and BH12 used in Comparative Example 3 also have the same backbone structure. In this case, BH1 was introduced by introducing additional substituents after deuterium had already been substituted during the synthesis of anthracene using benzene-d6 deuterized in a bottom-up manner. 99% of the 8 substitution positions based on anthracene were substituted with deuterium, and 30.7% of the 26 substitution positions based on the entire BH10 compound were substituted with deuterium. Meanwhile, BH12 was prepared by synthesizing BH10 through Comparative Synthesis Example 1, and then substituting deuterium into BH10 through a deuteration process through Comparative Synthesis Example 3. As a result, 91% of the 8 substitution positions based on anthracene were substituted with deuterium, and 87% of the 26 substitution positions based on the entire BH10 compound were substituted with deuterium. As a result, it can be confirmed that Comparative Example 3 using BH12 with a high deuterium conversion rate based on all compounds has a longer life than Example 1, but Example 1 has a deuterium conversion rate of 30.7% based on all compounds, but shows a life effect of 95% ((175 / 185) x 100) of the life of Comparative Example 3 with a deuterium conversion rate of 87% based on all compounds. In addition, BH1 in Example 1 directly synthesizes anthracene using benzene-d6 that is already highly deuterated, so no separate deuteration process is performed, simplifying the process and improving the life via deuterated anthracene with high efficiency.

[0228] This effect can also be confirmed by comparing BH2 used in Example 2 with BH13 used in Comparative Example 4. Specifically, it can be confirmed that Example 2, although the deuterium conversion rate based on all compounds is 36%, exhibits a life effect that is 96% ((186 / 194) x 100) of the life effect of Comparative Example 3, in which the deuterium conversion rate based on all compounds is 85%.

Claims

1. A method for preparing a deuterated anthracene compound, comprising the steps of: reacting a halogenated benzene having at least one deuterium with a compound represented by the following formula 1 to synthesize a deuterated anthracene compound: [Chemical formula 1] 【Chemistry 1】 In the above Chemical Formula 1, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

2. A method for preparing a deuterated anthracene compound, comprising reacting a halogenated benzene-d5 with a compound represented by the following formula 1 to synthesize a compound represented by the following formula 2: [Chemical formula 1] 【Chemistry 2】 [Chemical formula 2] 【Chemistry 3】 In the above Chemical Formulas 1 and 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; b is an integer from 1 to 8.

3. 2. The method for producing a deuterated anthracene compound according to claim 1, wherein the halogenated benzene having at least one deuterium is halogenated benzene-d5.

4. The method for producing the deuterated anthracene compound according to any one of claims 1 to 3, wherein the deuterated anthracene compound is a compound represented by the following formula 2: [Chemical formula 2] 【Chemistry 4】 In the above Chemical Formula 2, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; b is an integer from 1 to 8.

5. synthesizing a compound of the following formula 3 using a compound of the formula 2 in which Ar2 is hydrogen and a solution containing a halogen donor; and The method for preparing the deuterated anthracene compound according to claim 2 or 4, comprising reacting the compound represented by Formula 3 with L-Ar2 to synthesize a compound represented by Formula 4: [Chemical formula 3] 【Chemistry 5】 [Chemical formula 4] 【Chemistry 6】 In the formulas 3 and 4, Ar1 and Ar2 are the same or different and each independently represents deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; X is a halogen group and L is a leaving group; b is an integer from 1 to 8.

6. The method for producing a deuterated anthracene compound according to claim 1 or 3, further comprising the step of synthesizing a halogenated benzene-d5 from benzene-d6 using a halogen donor before the step of synthesizing the deuterated anthracene compound.

7. The method for producing a deuterated anthracene compound according to any one of claims 1 to 6, wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] 【Chemistry 7】 [Chemical formula 1-2] 【Chemistry 8】 [Chemical formula 1-3] 【Chemistry 9】 In the above Chemical Formulas 1-1 to 1-3, Y is CRaRb, NRc, O or S; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ra, Rb, Rc, and R1 to R3 are the same or different and each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; r1 and r2 are each an integer from 1 to 7, and r3 is an integer from 1 to 5; When r1 is 2 or more, R1 are the same or different, When r2 is 2 or more, R2 are the same or different, When r3 is 2 or more, R3 are the same or different.

8. The method for producing a deuterated anthracene compound according to claim 1 or 2, wherein the chemical formula 1 is any one of the following structures: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 。

9. The step of synthesizing the compound of Formula 2 includes: The method for preparing a deuterated anthracene compound according to claim 2 or 4, wherein the compound of Chemical Formula 2 is synthesized using a solution containing halogenated benzene-d5, the compound of Chemical Formula 1, 2,2,6,6-tetramethylpiperidine, an alkyl lithium, and an ether solvent.

10. The method for producing a deuterated anthracene compound according to claim 2 or 4, wherein the chemical formula 2 is any one of the following structures: 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 Here, b is an integer from 1 to 8.

11. The method for producing a deuterated anthracene compound according to claim 5, wherein the chemical formula 3 is any one of the following structures: 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 Here, b is an integer from 1 to 8.

12. The method for producing a deuterated anthracene compound according to claim 5, wherein the chemical formula 4 is any one of the following structures: 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical Formula 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 Here, b is an integer from 1 to 8.

13. A reaction composition for a reaction to synthesize a deuterated anthracene compound, comprising a halogenated benzene having at least one deuterium and a compound of the following formula 1: [Chemical formula 1] 【Chemistry 52】 In the formula 1, Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

14. The reaction composition for a reaction for synthesizing a deuterated anthracene compound according to claim 13, wherein the halogenated benzene having at least one deuterium is halogenated benzene-d5.

15. The reaction composition for a reaction for synthesizing a deuterated anthracene compound according to claim 13 or 14, wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] 【Chemistry 53】 [Chemical formula 1-2] 【Chemical 54】 [Chemical formula 1-3] 【Chemistry 55】 In the above Chemical Formulas 1-1 to 1-3, Y is CRaRb, NRc, O or S; Ar2 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; Ra, Rb, Rc, and R1 to R3 are the same or different and each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; r1 and r2 are each an integer from 1 to 7, and r3 is an integer from 1 to 5; When r1 is 2 or more, R1 are the same or different, When r2 is 2 or more, R2 are the same or different, When r3 is 2 or more, R3 are the same or different.

16. The chemical formula 1 is a reaction composition for a reaction for synthesizing the deuterated anthracene compound according to any one of claims 13 to 15, which has any one of the following structures: 【Chemistry 56】 【Chemistry 57】 【Chemistry 58】 。

17. A reaction composition for a reaction for synthesizing the deuterated anthracene compound according to any one of claims 13 to 16, further comprising 2,2,6,6-tetramethylpiperidine, an alkyl lithium, and an ether solvent.

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