WO2021049889A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2021049889A1
WO2021049889A1 PCT/KR2020/012249 KR2020012249W WO2021049889A1 WO 2021049889 A1 WO2021049889 A1 WO 2021049889A1 KR 2020012249 W KR2020012249 W KR 2020012249W WO 2021049889 A1 WO2021049889 A1 WO 2021049889A1
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substituted
unsubstituted
group
formula
deuterium
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French (fr)
Korean (ko)
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김선우
홍완표
금수정
김명곤
김경희
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주식회사 엘지화학
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Priority to CN202080030525.3A priority Critical patent/CN113727985B/zh
Publication of WO2021049889A1 publication Critical patent/WO2021049889A1/ko

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Definitions

  • the present specification relates to a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Chinese Patent Publication 108586441
  • a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same are provided.
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Obviously,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boro
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,
  • r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,
  • r4 is an integer of 1 or 2
  • n is an integer of 1 or 2
  • r4+n is an integer of 2 or 3
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,
  • the compounds described herein can be used as a material for an organic material layer of an organic light-emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or improve lifespan characteristics in an organic light-emitting device.
  • the compounds described herein may be used as a hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.
  • the present Chemical Formula 1 has an effect of improving the conjugation and stability of the compound by including an alkyl group substituted with deuterium.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7 and a cathode 11 are sequentially stacked.
  • FIG. 2 shows a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, and
  • An example of an organic light-emitting device in which the first electron transport layer 8, the second electron transport layer 9, the electron injection layer 10, and the cathode 11 are sequentially stacked is shown.
  • the present invention provides a compound containing an alkyl group having 1 to 3 carbon atoms substituted with deuterium, and an organic light emitting device including the same. Since the CD bond of the compound of the present invention is stronger than that of the CH bond, the stability of the compound can be improved. When the chemical decomposition of the luminescent compound involves the destruction of the relatively weak C(sp 3 )-H bond, there is an effect of further improving the stability of the compound by using a stronger CD bond than the CH bond.
  • an alkyl group is used as a substituent capable of donating electrons, it is possible to effectively control the luminescence characteristics, but the introduced alkyl group is removed in a high energy state and decomposition of the compound occurs, resulting in a problem in the lifetime characteristics of the overall device.
  • the methyl radical, ethyl radical, and propyl radical which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to tertiary carbon radicals (more than 4 carbon atoms ), the bond of C(sp 3 )-C(sp 2 ) is destroyed and the resulting compound There is an effect that the decomposition process is relatively suppressed. Therefore, in the case of using an alkyl group having 1 to 3 carbon atoms substituted with deuterium, it is possible to effectively control the light emission characteristics while securing the stability of the blue device.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group (-CN); Nitro group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; Halogen group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • substituted or unsubstituted with A, B or C means that one or more groups selected from the group consisting of substituents A to C or two or more groups selected from the group are substituted or unsubstituted with a linked group.
  • substituted or unsubstituted with -CC may be substituted or unsubstituted with -ABC, may be substituted or unsubstituted with -BCA, may be unsubstituted or substituted with -AAB, or -A-(C ) It may be substituted or unsubstituted with 2 , and is not limited to the above exemplified bar.
  • N% substitution with deuterium means that N% of the hydrogen available in the structure is substituted with deuterium. For example, supposing that 25% of dibenzofuran is substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran have been substituted with deuterium.
  • the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC/MS.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. Does not.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • 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 an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.
  • the alkoxy group may be a straight chain, branched chain, or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms.
  • Substituents including an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include all of the straight chain or branched form.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.
  • the amine group is -NH 2 , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted in the amine group.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms.
  • substituted amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine Group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • aryl group in the aryloxy group may be described above with respect to the aryl group.
  • alkyl group in the alkylthio group and the alkylsulfonyl group.
  • the description of the aryl group described above may be applied to the aryl group in the arylthio group and the arylsulfonyl group.
  • the above-described description of the alkyl group may be applied to the alkyl group in the alkyl thioxy group and the alkyl sulfoxy group.
  • the description of the aryl group described above may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.
  • the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, and the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • ring in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group, except that it is a monovalent group.
  • the meaning of forming a ring by bonding with adjacent groups to each other means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups;
  • the hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring including at least one selected from N, O, P, S, Si and Se.
  • the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring refers to a ring that is not aromatic and includes only carbon and hydrogen atoms.
  • Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.
  • the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms.
  • aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto.
  • the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.
  • the aromatic heterocycle means an aromatic ring containing at least one heteroatom.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothi
  • the present specification provides a compound represented by the following formula (1).
  • the compound represented by the following formula (1) is used in the organic material layer of the organic light-emitting device, the efficiency of the organic light-emitting device is improved, as well as a low driving voltage and excellent lifespan characteristics.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Obviously,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boro
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,
  • r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,
  • r4 is an integer of 1 or 2
  • n is an integer of 1 or 2
  • r4+n is an integer of 2 or 3
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,
  • the half width of the compound represented by Formula 1 is 17 nm to 35 nm.
  • the alkyl group having 1 to 3 carbon atoms substituted with deuterium is -CDH 2 ; -CD 2 H; -CD 3 ; -C 2 D 5 ; -CH 2 CD 3 ; -CD(CD 3 ) 2 ; Alternatively, it may be represented by -CH(CD 3 ) 2.
  • a methyl group substituted with deuterium may be represented by -CD 3.
  • the ethyl group substituted with deuterium may be represented by -C 2 D 5 (-CD 2 CD 3 ) or CH 2 CD 3.
  • the propyl group substituted with deuterium (-CD(CD 3 ) 2 ) or It can be expressed as (CH(CD 3 ) 2 ). Means the bonding position.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring condensed ring of aromatic hydrocarbon ring.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a condensed ring of a monocyclic or bicyclic aromatic hydrocarbon ring.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • A1 and A2 are the same as or different from each other, and each independently a benzene ring unsubstituted or substituted with a phenyl group or a naphthyl group; A substituted or unsubstituted fluorene ring; A substituted or unsubstituted triphenylene ring; A substituted or unsubstituted cyclohexane ring; A substituted or unsubstituted benzene ring condensed with a substituted or unsubstituted cyclopentene or a substituted or unsubstituted cyclohexene; Or a substituted or unsubstituted dibenzofuran ring.
  • A1 and A2 are the same as or different from each other, and each independently is represented by any one of the following Chemical Formulas A100 to A103.
  • G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • X11 is O; S; Or CR101R102,
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • g1 is an integer from 0 to 5
  • g1' is an integer from 0 to 11
  • g1'' is an integer from 0 to 7
  • g1''' is an integer from 0 to 11
  • a1 is an integer of 1 to 2
  • g1', g1'' and g1''' are each 2 or more, 2 or more G1s are the same as or different from each other,
  • G1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or combine with an adjacent group to form a substituted or unsubstituted ring.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring combined with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 4 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring by bonding with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or a butyl group substituted or unsubstituted with deuterium, or a phenanthrene ring by bonding with an adjacent group to form a phenanthrene ring, or a carbazole ring by directly bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or a t-butyl group substituted or unsubstituted with deuterium, or bonded to an adjacent group to form a phenanthrene ring, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • X11 is O; Or CR101R102.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R101 and R102 are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Or an aryl group unsubstituted or substituted with deuterium.
  • R101 and R102 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R101 and R102 are methyl groups unsubstituted or substituted with deuterium.
  • R101 and R102 is a methyl group; Or CD 3 .
  • a1 is 1 or 2.
  • g1 is 1 to 4.
  • g1' is 1 to 4.
  • g1'' is 1 to 4.
  • g1"' is 1 to 4.
  • A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • R101 to R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R103 is a substituted or unsubstituted aryl group.
  • R103 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R103 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R103 is an aryl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.
  • R103 is a phenyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.
  • R103 is a phenyl group unsubstituted or substituted with CD 3.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • G101 and G102 are the same as or different from each other, and each independently a deuterium-substituted or unsubstituted alkyl group.
  • G101 and G102 are methyl groups; Or CD 3 .
  • A1 and A2 are the same as or different from each other, and each independently a benzene ring; Triphenylene ring; Fluorene ring; Cyclohexane ring; Dibenzofuran ring; Benzene ring condensed with cyclopentene; Or a benzene ring condensed with cyclohexane, and the substituents are unsubstituted or substituted with G1.
  • A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • the groups are deuterium; Or it is unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C20 alkyl group, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium, or through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or a propyl group unsubstituted or substituted with deuterium.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or an i-propyl group unsubstituted or substituted with deuterium.
  • X1 and X2 are -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected through.
  • X1 and X2 are directly connected through -CRaRb-, -NRc-, -O-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; An alkenyl group unsubstituted or substituted with deuterium; An alkynyl group unsubstituted or substituted with deuterium; Arylalkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring with a methyl group substituted with deuterium or deuterium.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 30 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with deuterium or a substituted or unsubstituted heterocycle.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium or CD 3; Aryl group unsubstituted or substituted with deuterium or CD 3; Or deuterium, or substituted with a CD 3 or unsubstituted heterocyclic group, or form a substituted or unsubstituted heterocyclic group with the adjacent deuterium or CD 3 groups are bonded to each other to a substituted or unsubstituted aromatic hydrocarbon ring or a deuterium or CD 3 ring do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted fluorene ring; Or it forms the following structure which is substituted or unsubstituted.
  • Ra To Rh are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a methyl group, and a hexahydrocarbazole group, or a group to which two or more are connected, or adjacent groups are bonded to each other to form a fluorene ring; Or to form the following structure.
  • the following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3, Means a position to form a ring.
  • Ra To Rh are the same as or different from each other, and each independently CD 3 ; Methyl group; Or a phenyl group unsubstituted or substituted with a hexahydrocarbazole group substituted with CD 3 or CD 3 , or adjacent groups bonded to each other to form a fluorene ring; Or to form the following structure.
  • the following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3, Means a position to form a ring.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substitute
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; A substituted or unsubstituted C1 to C20 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms; A substituted or unsubstituted C1 to C10 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 14 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 14 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An aryloxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkylthio group unsubstituted
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted methylthio group; A substituted or unsubstituted phenylthio group; A substituted or unsubstituted methylsulfonyl group; A substituted or unsubstituted t-butylsulfonyl group; A substituted or unsubstituted phenylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted trimethylsilyl
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R1 and R2 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium or -F; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with deuterium or -F; A pentyl group unsubstituted or substituted with deuterium or -F; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; A phenylthio group unsubstituted or substituted with deuterium, a methyl
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; Phenylthio group; A methylsulfonyl group unsubstituted or substituted with deuterium; T-butylsulfonyl group unsubstituted or substituted with deuterium; Phenyl
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; Deuterium, -F, a phenyl group unsubstituted or substituted with a methyl group or CD 3 or an amine group substituted with a CD 3; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuteruter
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phenylpropyl group; A substituted or unsubstituted adamantyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazole group, or a direct bond with R1 or R
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R3 and R5 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; An ethyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group; Diphenylboron group; A phenylpropyl group unsubstituted or substituted with deuterium; Adamantyl group; Deuterium, -F, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; A phenylpropyl group unsubstituted or substituted with deuterium; Or deuterium, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted with deuterium, or a direct bond with R1 or R2; Or an indene ring unsubstit
  • adjacent R1 and R3 combine with each other to form a substituted or unsubstituted ring.
  • adjacent R1 and R3 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B Form a ring
  • adjacent R1 and R3 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3 Form a ring
  • adjacent R1 and R3 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.
  • adjacent R2 and R5 combine with each other to form a substituted or unsubstituted ring.
  • adjacent R2 and R5 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B Form a ring
  • adjacent R2 and R5 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3 Form a ring
  • adjacent R2 and R5 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.
  • R1 to R5 are represented by -L-R11,
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C 1 to C 20 alkylene group; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C1-C10 alkylene group; Or a substituted or unsubstituted C6 to C10 arylene group.
  • L is a direct bond; O; S; SO 2 ; Or a substituted or unsubstituted C 1 to C 5 alkylene group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted methylene group; Or a substituted or unsubstituted methylene group is a propylene group.
  • L is a direct bond; O; S; SO 2 ; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.
  • L is a direct bond; O; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C1 to C20 haloalkyl group; A substituted or unsubstituted amine group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted amine group having 1 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; CD 3 ; CF 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.
  • R11 is hydrogen; heavy hydrogen; CD 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring bonded to each other with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or it forms a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.
  • R1 or R2 is a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring by bonding with an adjacent group to each other; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring aromatic hydrocarbon ring to form a condensed ring.
  • R1 or R2 is a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring by bonding to each other with adjacent groups; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a monocyclic or bicyclic aromatic hydrocarbon ring.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms is formed.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms is formed.
  • R1 or R2 is each directly bonded to R3 or R5, bonded through B substituted with a substituted or unsubstituted phenyl group, or bonded to an adjacent group through a substituted or unsubstituted phenanthrene.
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R1 or R2 is directly bonded to R3 or R5, respectively, or by bonding with an adjacent group to each other to form a substituted or unsubstituted indene ring; A substituted or unsubstituted benzofuran ring; Substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; Or a substituted or unsubstituted tetrahydroethanonaphthalene ring is formed.
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, butyl group, and phenyl group, or a group to which two or more groups are bonded.
  • R1 or R2 when R1 or R2 is bonded to an adjacent group to form a substituted or unsubstituted ring, R1 or R2 is directly bonded to R3 or R5 to form a carbazole ring; Or it forms a hexahydrocarbazole ring, or is connected through B Includes the case of forming a ring.
  • the rings are substituted or unsubstituted.
  • the ring when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, the ring is represented by any one of the following formulas C1 to C3.
  • X21, X22 and X31 are the same as or different from each other, and each independently O; S; CP11P12; Or NP13,
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • b1 is an integer of 1 to 3
  • p1 is an integer of 0 to 10
  • p2 and p3 are each an integer of 0 to 4,
  • X21 and X22 are the same as or different from each other, and each independently, O; S; Or CP11P12.
  • X31 is O; S; CP11P12; Or NP13.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; 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, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted C 3 to C 30 aliphatic hydrocarbon ring is formed.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; 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, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with deuterium; It is a phenyl group, or combines with an adjacent group to form a benzene ring substituted or unsubstituted with an alkyl group substituted or unsubstituted with deuterium or deuterium, or a bicycloheptane ring or a bicyclooctane ring.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group, or a benzene ring unsubstituted or substituted with a methyl group unsubstituted or substituted with deuterium or deuterium by bonding to each other with an adjacent group, or a bicycloheptane ring or a bicyclooctane ring.
  • b1 is 1 or 2.
  • p1 is an integer of 1 to 6.
  • p1 is an integer of 1 to 4.
  • p2 and p3 are integers of 1 to 4.
  • R1 or R2 when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, it is represented by one of the following structures.
  • * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.
  • the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or substituted or unsubstituted with deuterium substituted or unsubstituted butyl group.
  • the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or it is unsubstituted or substituted with a t-butyl group substituted or unsubstituted with deuterium.
  • the structures are deuterium; Or it is substituted or unsubstituted with CD 3.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least two of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.
  • At least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least three of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R5 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least two of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least three of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least one of R1 to R5 is CD 3 .
  • At least two of R1 to R5 are CD 3 .
  • At least three of R1 to R5 are CD 3 .
  • R4 are the same or different and each is independently hydrogen or CD from each other - is 3 -
  • Chemical Formula 1 may be represented by Chemical Formula 101 below.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or it is represented by the following formula 2.
  • Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.
  • Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.
  • Y is CDH 2 ; CD 2 H; CD 3 ; C 2 D 5 ; CH 2 CD 3 ; CD(CD 3 ) 2 ; Or CH(CD 3 ) 2 .
  • Y is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is either CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • Y is CDH 2 ; It is either CD 2 H or CD 3.
  • Y is CD 3 .
  • Y is represented by the following formula (2).
  • B1 and B2 are the same as or different from each other, and each independently an aliphatic hydrocarbon ring; Or an aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r6 and r7 are the same as or different from each other, and each independently an integer of 1 to 11, and when r6 and r7 are each 2 or more, the substituents in each parenthesis are the same or different from each other,
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.
  • B1 and B2 are the same as or different from each other, and each independently a benzene ring or a cyclohexane ring unsubstituted or substituted with CD 3.
  • B1 and B2 are benzene rings.
  • B1 is a benzene ring
  • B2 is a cyclohexane ring unsubstituted or substituted with CD 3.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium or CD 3 , or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a deuterium, methyl group, CD 3 or t-butyl group; Or cyclohexene unsubstituted or substituted with deuterium, methyl group, CD 3 or t-butyl group to form a hexahydro
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or a phenyl group, R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring, or to form a methyl group substituted or unsubstituted cyclohexene ring by bonding to each other with adjacent groups.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or, it is a phenyl group, or combines with an adjacent group to form the following structure.
  • the following structure is unsubstituted or substituted with deuterium, a methyl group unsubstituted or substituted with deuterium, an i-propyl group or t-butyl group substituted or unsubstituted with deuterium, Means a position bonded to the formula (1).
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; Methyl group; CD 3 ; Or a t-butyl group, or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; Or a t-butyl group, R6 and R7 are bonded to each other to CD 3 substituted or unsubstituted carbazole ring; Or CD 3 to form a substituted or unsubstituted hexahydrocarbazole ring.
  • Y when Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • R1 to R7 when Y is represented by Formula 2, at least one of R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least two of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least three of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R7 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least two of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least three of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least one of R1 to R7 is CD 3 .
  • At least two of R1 to R7 are CD 3 .
  • At least three of R1 to R7 are CD 3 .
  • r1 and r2 are the same as or different from each other, and are each independently an integer of 1 to 3.
  • r1 and r2 are the same as or different from each other, and are each independently 1 or 2.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 11.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 9.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 5.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 3.
  • r4 is an integer of 1 or 2.
  • r4 is 1.
  • r4 is 2.
  • n is an integer of 1 or 2.
  • n 1
  • n is 2.
  • r4+n is an integer of 2 or 3.
  • Formula 2 ( ) Is represented by any one of the following Chemical Formulas 201 to 203.
  • G6 and G7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
  • g6 and g7 are each an integer of 1 to 5, g6' and g7' are an integer of 1 to 4, and g7'' is an integer of 1 to 8,
  • G6 and G7 are the same as those of R6 and R7 described above.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 20 alkyl group.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 10 alkyl group.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium.
  • G16 and G17 are methyl groups or CD 3 .
  • Chemical Formula 2 is represented by any one of the following structural formulas.
  • g6, g7, g6', g7', and g7'' are integers of 1 to 4, respectively.
  • g6, g7, g6', g7', and g7'' are integers of 1 to 3, respectively.
  • g6, g7, g6', g7', and g7'' are 1 or 2, respectively.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.
  • R1 to R7 A1, A2, B1, B2, X1, X2 and r1 to r7 are the same as those in Formula 1,
  • Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • n is an integer of 1 or 2
  • Z is the same as or different from each other
  • r4+m is an integer of 2 or 3.
  • Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.
  • Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.
  • Z is a methyl group substituted with deuterium.
  • Z is CDH 2 ; It is either CD 2 H or CD 3.
  • Z is CD 3 .
  • m is an integer of 1 or 2.
  • m is 1.
  • m is 2.
  • At least one of X1, X2, and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R5 in Formula 1-1 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • Formula 1 is represented by any one of the following Formulas 1-3 to 1-7.
  • R1 to R7, X1, X2 and r1 to r7 are the same as those in Formula 1,
  • Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • n is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-8.
  • A1, A2, R1 to R5, r1 to r5, Y and n are the same as those in Formula 1,
  • X3 is CRaRb, NRc, O, PRd, S, PORe, SO 2 , SiRfRg or BRh,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
  • Ra to Rh in Formula 1-8 is the same as the definition of Ra to Rh in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-9 or 1-10.
  • X1, X2, A1, A2, R1, R3 to R5, r1, r3 to r5, Y and n are the same as those in Formula 1,
  • A3 and A4 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • r21 and r22 are each an integer of 1 to 9,
  • R21 and R22 are each 2 or more, two or more R21 and R22 are each the same as or different from each other.
  • A3 is represented by any one of the following structural formulas.
  • the definition of a case where R1 or R2 is bonded to each other to form a substituted or unsubstituted ring is applied to A3 and A4.
  • A3 and A4 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.
  • Chemical Formula 1 is represented by the following Chemical Formulas 1-11 or 1-12.
  • X1, X2, R1 to R5, r1, r3, r4, A1, Y and n are the same as those in Formula 1,
  • X101 is a direct bond; Or -BR103-,
  • R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • r2' is 1 or 2
  • r5' is an integer from 1 to 4,
  • r5'' is an integer from 1 to 8
  • R2 and R5 are each 2 or more, two or more R2 and R5 are each the same as or different from each other.
  • Formula 1 is represented by any one of the following compounds.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.
  • the compound of Formula 1 of the present invention may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.
  • a deuterium substituted methyl group may be introduced from [Intermediate 3], which is a boron compound containing a methyl group, using a deuterium substitution reaction using a transition metal catalyst.
  • Intermediate 3 is a boron compound containing a methyl group, using a deuterium substitution reaction using a transition metal catalyst.
  • Reaction Scheme 3 a chemical substance having a methyl group at a specific position is illustrated, but a deuterium substituted alkyl group may be introduced by replacing the C-H bond of the alkyl groups present at various positions of the boron compound in addition to the methyl group to a C-D bond with a substitution rate of 15% or more.
  • the conjugation length and energy band gap of the aforementioned chemicals are closely related. Specifically, the longer the conjugation length of the chemical, the smaller the energy band gap.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound are adjusted, and the CH bond of the methyl group among the introduced substituents is changed to a harder CD bond, thereby optical properties and lifetime.
  • Compounds with improved properties can be synthesized.
  • the present specification provides an organic light-emitting device including the above-described compound.
  • the first electrode A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device 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, an electron blocking layer, a hole blocking layer, etc. as an organic material layer. have.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 above.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a blue fluorescent dopant of the emission layer.
  • the organic material layer includes a hole injection layer or a hole transport layer
  • the hole injection layer or the hole transport layer includes the compound represented by Formula 1 above.
  • the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons
  • the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons is the formula Including the compound represented by 1.
  • the organic material layer includes an electron blocking layer
  • the electron blocking layer includes the compound represented by Formula 1 above.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes a compound represented by Formula 1 above.
  • the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the emission layer further includes a host compound.
  • the emission layer further includes a host compound, and the host compound is one in which at least one hydrogen is substituted with deuterium.
  • the host compound when the host compound is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by 40% or more with deuterium. In another exemplary embodiment, the host compound is substituted with deuterium by at least 60%. In another exemplary embodiment, the host compound is 80% or more substituted with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
  • the emission layer further includes a compound represented by the following formula (H).
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r20 is an integer from 0 to 8, and when r20 is 2 or more, R20 is the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 40 carbon atoms; Or it is a C6-C40 divalent heterocyclic group.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 20 carbon atoms; Or a divalent heterocyclic group having 6 to 20 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently 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 anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsub
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthobenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.
  • R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; Fluorine group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C 3 to C 10 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • R20 is hydrogen; heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.
  • r20 is an integer of 1 to 8.
  • Chemical Formula H may include at least one deuterium.
  • Chemical Formula H is represented by the following Chemical Formula I or J.
  • the structure of Formula H when the compound represented by Formula H is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the structure of Formula H is substituted by 40% or more with deuterium. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by at least 60%. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by 80% or more. In another exemplary embodiment, the structure of Formula H is 100% substituted with deuterium.
  • the compound represented by Formula H is any one selected from the following compounds.
  • the compound represented by Formula 1 is used as a dopant, and the compound represented by Formula H is used as a host.
  • the content of the dopant may be selected from 0.01 to 10 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
  • the emission layer further includes two or more host compounds.
  • the content of the host may be 10:90 to 90:10 based on a first host: a second host.
  • the content between the hosts may be 20:80 to 80:20, and in another example, it may be 40:60 to 60:40.
  • the light-emitting layer may further include a host material, and the host may include a condensed aromatic ring derivative or a heterocyclic-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.
  • the organic light emitting device includes a first electrode; A second electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Formula 1 above.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.
  • materials other than the compound represented by Formula 1 may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant those known in the art may be used, for example, a metal or a metal complex.
  • the electron transport layer including the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of two or more hole transport layers.
  • the organic material layer further comprises a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 Can include.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 7 and a cathode 11 are sequentially stacked.
  • the compound may be included in the emission layer 3.
  • the compound includes the first hole injection layer 3, the second hole injection layer 4, the hole transport layer 5, the electron blocking layer 6, the light emitting layer 7, and the first electron transport layer ( 8), it may be included in one or more of the second electron transport layer 9 and the electron injection layer 10.
  • the organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • It can be manufactured by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb;
  • Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the second electrode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes in addition to the compound represented by Formula 1 above.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto.
  • examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • the emission material of the emission layer is formed by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • a material capable of emitting light in the visible region a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxy-quinoline aluminum complex Alq3
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds Poly(p-phenylenevinylene) (PPV)-based polymer
  • Spiro compounds Polyfluorene; And rubrene, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole injection effect in the first electrode and an excellent hole injection effect in the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Carbazole-based organic matter; Nitrile-based organics; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of two or more of the above examples, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transporting material is a material capable of transporting holes from the first electrode or the hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of receiving electrons from the second electrode and transferring them to the light emitting layer, and a material having high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives; LiQ and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired first electrode material, as used according to the prior art.
  • a suitable first electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from an electrode. It is preferable that the electron injection material is excellent in the ability to transport electrons, and has an electron injection effect from the second electrode and an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • metal complex compounds and nitrogen-containing 5-membered ring derivatives and mixtures of two or more of the above examples, but are not limited thereto.
  • 8-hydroxyquinolinato lithium bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer.
  • Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that prevents holes from reaching the second electrode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but are not limited thereto.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the compound according to the present specification may act on a principle similar to that applied to an organic light-emitting device in an organic light-emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor.
  • the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.
  • a glass substrate coated with a thin film of 1,400 ⁇ of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A and HI-B were thermally vacuum deposited to a thickness of 650 ⁇ and 50 ⁇ , respectively, to form a first hole injection layer and a second hole injection layer.
  • the following HT-A was vacuum deposited to a thickness of 600 ⁇ to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • a light emitting layer was formed by vacuum deposition of Compound 1 as a blue light-emitting dopant on the electron blocking layer to a thickness of 4 wt% based on the total weight of the light-emitting layer and BH-1 as a host to a thickness of 96 wt% and 200 ⁇ based on the total weight of the light-emitting layer.
  • ET-A was vacuum-deposited on the light-emitting layer as a first electron transport layer, and subsequently ET-B and LiQ were vacuum-deposited at a 1:1 weight ratio to form a second electron transport layer having a thickness of 360 ⁇ .
  • LiQ was vacuum-deposited on the second electron transport layer and vacuum-deposited to a thickness of 5 ⁇ to form an electron injection layer.
  • the deposition rate of organic materials was maintained at 0.4 ⁇ 0.9 ⁇ /sec, and the deposition rate of aluminum at the cathode was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr.
  • the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr.
  • Example 1 Examples 2 to 20 and Comparative Examples 1 to 1 were used in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compounds 1 and BH-1 as the dopant and host of the emission layer. Each of the organic light emitting devices of 4 was manufactured.
  • T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.
  • Example 1 the same method as in Example 1 was used, except that the compound shown in Table 2 was used instead of the compound 1 as the dopant of the light emitting layer, and the compound shown in Table 2 was used as the host of the light emitting layer.
  • Organic light emitting devices of Examples 21 to 24 and Comparative Example 5 were fabricated, respectively.
  • the weight ratio of the first host and the second host of the emission layer is 50:50.
  • T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.
  • the conversion efficiency (cd/A/y) considers from the current efficiency (cd/A) to the color purity (CIEy) of the material, and becomes an important efficiency reference value in small and large organic light emitting devices aiming at high luminance and high color reproducibility. .
  • the organic light emitting device was constructed using a dopant material including an alkyl group having 1 to 3 carbon atoms substituted with deuterium represented by [Chemical Formula 1] according to an exemplary embodiment of the present specification. At that time, both the conversion efficiency and lifetime performance of the device were superior to those of the other devices.
  • the compound of Formula 1 of the present invention is characterized in that an alkyl group substituted with deuterium is bonded at a specific position, and the efficiency is up to about 10% compared to the comparative compounds BD-A, BD-C and BD-D that are not otherwise. The results were high, and the lifespan was 2 to 3 times higher.
  • the compound of Formula 1 including an alkyl group having 1 to 3 carbon atoms substituted with deuterium exhibited excellent effects in efficiency and life as compared to Comparative Example BD-B including a butyl group substituted with deuterium.
  • methyl radical, ethyl radical, and propyl radical which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to the butyl radical, which is a tertiary carbon radical (more than 4 carbon atoms), and the C(sp 3 )-C(sp 2 ) bond is destroyed This is because the decomposition process of the compound that occurs is relatively suppressed, and the stability of the compound structure is ensured.

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Cited By (6)

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WO2021213972A1 (en) * 2020-04-22 2021-10-28 Cynora Gmbh Organic molecules for optoelectronic devices
WO2021255073A1 (en) * 2020-06-18 2021-12-23 Cynora Gmbh Organic molecules for optoelectronic devices
US20220093874A1 (en) * 2020-09-18 2022-03-24 Samsung Display Co., Ltd. Light emitting device and polycyclic compound for light emitting device
EP4215535A1 (en) 2022-01-24 2023-07-26 Idemitsu Kosan Co.,Ltd. Compound and an organic electroluminescence device comprising the compound
WO2024013709A1 (en) 2022-07-14 2024-01-18 Idemitsu Kosan Co., Ltd. Compound and an organic electroluminescence device comprising the compound
EP4326030A1 (en) * 2022-08-17 2024-02-21 Universal Display Corporation Organic electroluminescent materials and devices

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KR20220126480A (ko) * 2021-03-09 2022-09-16 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
CN114213439A (zh) * 2021-12-17 2022-03-22 湖北尚赛光电材料有限公司 一种杂环化合物及其有机电致发光器件
WO2024104383A1 (zh) * 2022-11-15 2024-05-23 浙江光昊光电科技有限公司 一种含苯并菲的有机化合物及其在有机光电器件中的应用

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WO2021213972A1 (en) * 2020-04-22 2021-10-28 Cynora Gmbh Organic molecules for optoelectronic devices
WO2021255073A1 (en) * 2020-06-18 2021-12-23 Cynora Gmbh Organic molecules for optoelectronic devices
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EP4326030A1 (en) * 2022-08-17 2024-02-21 Universal Display Corporation Organic electroluminescent materials and devices

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