Patent Application
20220348597
The present specification relates to an organic light emitting device.
An organic light emission phenomenon generally refers to a phenomenon converting electrical energy to light energy using an organic material. An organic light emitting device using an organic light emission phenomenon normally has a structure including an anode, a cathode, and an organic material layer therebetween. Herein, the organic material layer is often formed in a multilayer structure formed with different materials in order to increase efficiency and stability of the organic light emitting device, and for example, may be formed with a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer, an electron injection layer and the like. When a voltage is applied between the two electrodes in such an organic light emitting device structure, holes and electrons are injected to the organic material layer from the anode and the cathode, respectively, and when the injected holes and electrons meet, excitons are formed, and light emits when these excitons fall back to the ground state.
Development of new materials for such an organic light emitting device has been continuously required.
International Patent Application Laid-Open Publication No. 2016-152418
The present specification describes an organic light emitting device.
The present specification provides an organic light emitting device including an anode; a cathode; and an organic material layer provided between the anode and the cathode,
wherein the organic material layer includes a light emitting layer and a first organic material layer,
the first organic material layer is provided between the anode and the light emitting layer,
the light emitting layer includes a compound of the following Chemical Formula 1, and
the first organic material layer includes a compound of the following Chemical Formula 2.
In Chemical Formula 1,
X1 is O or S,
Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group of rings consisting of a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic heteroring; and a substituted or unsubstituted aliphatic heteroring, or a fused ring of two or more rings selected from the group of rings,
R1 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; an arylalkyl group unsubstituted or substituted with deuterium; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or adjacent groups of R1 bond to each other to form a substituted or unsubstituted ring, and
r1 is an integer of 0 to 3, and R1s are the same as or different from each other when r1 is 2 or greater,
in Chemical Formula 2,
L1 and L2 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,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R11 to R13 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or adjacent groups among R11 to R13 bond to each other to form a substituted or unsubstituted ring, and
r11 is an integer of 0 to 8, r12 and r13 are each an integer of 0 to 4, and substituents in the parentheses are the same as or different from each other when r11 to r13 are each 2 or greater.
By including a compound of Chemical Formula 1 in a light emitting layer and a compound of Chemical Formula 2 in a first organic material layer, an organic light emitting device described in the present specification has a low driving voltage, and has excellent efficiency properties and excellent lifetime. Specifically, low driving voltage, high efficiency and improved lifetime can be obtained by controlling a degree of hole and/or electron transfer through properly adjusting HOMO energy level and LUMO energy level.
1: Substrate/2: Anode/3: Hole Injection Layer/4: Hole Transfer Layer/4a: First Hole Transfer Layer/4b: Second Hole Transfer Layer/4c: Third Hole Transfer Layer/4d: Fourth Hole Transfer Layer/4e: Fifth Hole Transfer Layer/4f: Sixth Hole Transfer Layer/4p: P-doped Hole Transfer Layer/4pa: First P-doped Hole Transfer Layer/4R: Red Hole Transfer Layer/4G: Green Hole Transfer Layer/4B: Blue Hole Transfer Layer/5: Electron Blocking Layer/6: Light Emitting Layer/6a: First Light Emitting Layer/6b: Second Light Emitting Layer/6c: Third Light Emitting Layer/6BF: Blue Fluorescent Light Emitting Layer/6BFa: First Blue Fluorescent Light Emitting Layer/6BFb: Second Blue Fluorescent Light Emitting Layer/6BFc: Third Blue Fluorescent Light Emitting Layer/6YGP: Yellow Green Phosphorescent Light Emitting Layer/6RP: Red Phosphorescent Light Emitting Layer/6GP: Green Phosphorescent Light Emitting Layer/7: Hole Blocking Layer/8: Electron Injection and Transfer Layer/9: Electron Transfer Layer/9a: First Electron Transfer Layer/9b: Second Electron Transfer Layer/9c: Third Electron Transfer Layer/10: Electron Injection Layer/11: Cathode/12: N-type Charge Generating Layer/12a: First N-type Charge Generating Layer/12b: Second N-type Charge Generating Layer/13: P-type Charge Generating Layer/13a: First P-type Charge Generating Layer/13b: Second P-type Charge Generating Layer/14: Capping Layer
Hereinafter, the present specification will be described in more detail.
Chemical Formula 1 of the present disclosure includes a 5-membered heteroring including X1, and is capable of securing structural stability and superior electrochemical properties of the compound using sufficient electrons. Specifically, first triplet excitation energy of Chemical Formula 1 is lowered, and a difference between first singlet excitation energy and the first triplet excitation energy increases. Accordingly, triplet quenching is suppressed, and as a result, an organic light emitting device including the same has an increased lifetime.
Chemical Formula 2 of the present disclosure is an amine compound including carbazole and biphenylene groups (specifically, divalent group represented by [1,1′-biphenyl]-3,4′-diyl), and is capable of enhancing hole transferability and thermal stability, and is capable of enhancing light emission efficiency and accomplishing a long lifetime.
When using the compound of Chemical Formula 1 in a light emitting layer and using the compound of Chemical Formula 2 in a first organic material layer (specifically, hole transfer area), a hole transferable lamination structure may be protected from electrons not consumed in the light emitting layer while enhancing hole injection properties from an anode, and energy in an excited stated generating from the light emitting layer is prevented from spreading to the hole transferable lamination structure, and a charge balance of the whole device may be controlled.
In the present specification, a description of a certain part “including” certain constituents means capable of further including other constituents, and does not exclude other constituents unless particularly stated on the contrary.
In the present specification, a description of one member being placed “on” another member includes not only a case of the one member being in contact with the another member but a case of still another member being present between the two members.
In the present specification, * or a dotted line means a site bonding or fused to other substituents or bonding sites.
In the present specification, Cn means that the number of carbon atoms is n, and Cn-Cm means that the number of carbon atoms is from n to m.
Examples of substituents in the present specification are described below, however, the substituents are not limited thereto.
The term “substitution” means a hydrogen atom bonding to a carbon atom of a compound being changed to another substituent, and the position of substitution is not limited as long as it is a position at which a hydrogen atom is substituted, that is, a position at which a substituent may substitute, and when two or more substituents substitute, the two or more substituents may be the same as or different from each other.
In the present specification, a term “substituted or unsubstituted” means being substituted with one, two or more substituents selected from the substituent group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an aryl group; a heterocyclic group; a fused hydrocarbon ring group; and an amine group, or being substituted with a substituent from the substituent group which is further substituted by one or more selected from the substituent group above or by a combined group of two or more substituents selected therefrom, or having no substituents. In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the substituent group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C20 alkyl group; a C3-C60 cycloalkyl group; a C6-C60 aryl group; a C2-C60 heterocyclic group; a C9-C60 fused hydrocarbon ring group; and an amine group, or being substituted with a substituent from the substituent group which is further substituted by one or more substituents selected from the substituent group or by a combined group of two or more substituents therefrom, or having no substituents.
In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the substituent group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C10 alkyl group; a C3-C30 cycloalkyl group; a C6-C30 aryl group; a C2-C30 heterocyclic group; a C9-C30 fused hydrocarbon ring group; and an amine group, or being substituted with a substituent from the substituent group which is further substituted by one or more substituents selected from the substituent group or by a combined group of two or more substituents therefrom, or having no substituents.
In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the substituent group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C6 alkyl group; a C3-C20 cycloalkyl group; a C6-C20 aryl group; a C2-C20 heterocyclic group; a C9-C20 fused hydrocarbon ring group; and an amine group, or being substituted with a substituent from the substituent group which is further substituted by one or more selected from the substituent group or by a combined group of two or more substituents selected therefrom, or having no substituents.
In the present specification, “a substituent from the substituent group which is further substituted by one or more selected from the substituent group” refers to replacing hydrogen of the substituent with the one or more substituents selected from the substituent group. For example, a phenyl group may be further substituted by an isopropyl group, or an isopropyl group may be further substituted by a phenyl group to form a substituent of
respectively.
In the present specification, “a substituent from the substituent group which is further substituted by one or more selected from the substituent group or by a combined group of two or more substituents selected therefrom” includes not only (substituent 1)-(substituent 2)-(substituent 3), but also (substituent 2) and (substituent 3) to (substituent 1). For example, two phenyl groups and an isopropyl group may be linked to become a substituent of
The same rule described above also applies to linking four or more substituents.
In the present specification, “substituted with A or B” includes not only a case of being substituted with only A or substituted with only B, but also a case of being substituted with A and B.
Examples of the substituents are described below, however, the substituents are not limited thereto.
In the present specification, examples of the halogen group may include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
In the present specification, the silyl group may be represented by a chemical formula of —SiY11Y12Y13, and Y11, Y12 and Y13 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but are not limited thereto.
In the present specification, the boron group may be represented by a chemical formula of —BY14Y15, and Y14 and Y15 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group may include a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but are not limited thereto.
In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is from 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 6. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 4. Specific examples of the alkyl group may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group and the like, but are not limited thereto.
In the present specification, the alkoxy group means linking an alkyl group to an oxygen atom, and the alkylthio group means linking an alkyl group to a sulfur atom, and as the alkyl group in the alkoxy group and the alkylthio group, the description on the alkyl group provided above may be applied.
In the present specification, the amine group may be selected from the group consisting of —NH2; an alkylamine group; an alkylarylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group and a heteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 60. In the arylamine group, the number of carbon atoms is from 6 to 60. According to another embodiment, the number of carbon atoms of the arylamine group is from 6 to 40. Specific examples of the amine group may include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; an anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; an N-phenylnaphthylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; an N-phenylterphenylamine group; an N-phenanthrenylfluorenylamine group; an N-biphenylfluorenylamine group; an N-(4-(tert-butyl)phenyl)-N-phenylamine group; an N,N-bis(4-(tert-butyl)phenyl)amine group; an N,N-bis(3-(tert-butyl)phenyl)amine group and the like, but are not limited thereto.
In the present specification, the alkylamine group means an amine group in which N of the amine group is substituted with an alkyl group, and includes a dialkylamine group, an alkylarylamine group and an alkylheteroarylamine group.
In the present specification, the arylamine group means an amine group in which N of the amine group is substituted with aryl group, and includes a diarylamine group, an arylheteroarylamine group and an alkylarylamine group.
In the present specification, the heteroarylamine group means an amine group in which N of the amine group is substituted with a heteroaryl group, and includes a diheteroarylamine group, an arylheteroarylamine group and an alkylheteroarylamine group.
In the present specification, the alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
In the present specification, the arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.
In the present specification, the alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.
In the present specification, the alkyl group in the alkylamine group, the arylalkylamine group, the alkylthioxy group, the alkylsulfoxy group and the alkylheteroarylamine group is the same as the examples of the alkyl group. Specific examples of the alkylthioxy group may include a methylthioxy group; an ethylthioxy group; a tert-butylthioxy group; a hexylthioxy group; an octylthioxy group and the like, and specific examples of the alkylsulfoxy group may include mesyl; an ethylsulfoxy group; a propylsulfoxy group; a butylsulfoxy group and the like, however, the alkylthioxy group and the alkylsulfoxy group are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 6. The cycloalkyl group includes not only a monocyclic group, but also a bicyclic group such as a bridgehead, a fused ring or a spiro ring. Specific examples thereof may include 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 are not limited thereto.
In the present specification, the cycloalkene is a cyclic group that has a double bond present in the hydrocarbon ring but is not aromatic, and although not particularly limited thereto, the number of carbon atoms may be from 3 to 60, and according to one embodiment, the number of carbon atoms may be from 3 to 30. The cycloalkene includes not only a monocyclic group, but also a bicyclic group such as a bridgehead, a fused ring or a spiro ring. Examples of the cycloalkene may include cyclopropene, cyclobutene, cyclopentene, cyclohexene and the like, but are not limited thereto.
In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 20. When the aryl group is a monocyclic aryl group, examples thereof may include a phenyl group, a biphenyl group, a terphenyl group and the like, but are not limited thereto. Examples of the polycyclic aryl group may include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group and the like, but are not limited thereto.
In the present specification, a No. 9 carbon atom (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group and the like, and two substituents may bond to each other to form cyclopentane and a spiro structure such as fluorene.
In the present specification, the substituted aryl group may also include a form in which an aliphatic ring is fused to the aryl group. For example, a tetrahydronaphthalene group, a dihydroindene group and a dihydroanthracene group of the following structures are included in the substituted aryl group. In the following structures, one of the carbons of the benzene ring may be linked to other positions.
In the present specification, the fused hydrocarbon ring group means a fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, and has a form in which the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring are fused. The fused hydrocarbon ring group has 9 to 60, 9 to 30, 9 to 20, or 9 to 10 carbon atoms. Examples of the fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring may include a tetrahydronaphthalene group, a dihydroindene group and a dihydroanthracene group, but are not limited thereto.
In the present specification, the alkylaryl group means an aryl group substituted with an alkyl group, and may have substituents other than the alkyl group additionally linked thereto.
In the present specification, the arylalkyl group means an alkyl group substituted with an aryl group, and may have substituents other than the aryl group additionally linked thereto.
In the present specification, the aryloxy group means linking an aryl group to an oxygen atom, and the arylthio group means linking an aryl group to a sulfur atom, and as the aryl group in the aryloxy group and the arylthio group, the descriptions on the aryl group provided above may be applied. The aryl group in the aryloxy group is the same as the examples of the aryl group described above. Specific examples of the aryloxy group may include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group and the like, and examples of the arylthioxy group may include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like, however, the aryloxy group and the arylthioxy group are not limited thereto.
In the present specification, the heterocyclic group is a cyclic group including one or more of N, O, P, S, Si and Se as a heteroatom, and although not particularly limited thereto, the number of carbon atoms is preferably from 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 2 to 20. Examples of the heterocyclic group may include a pyridyl group; a quinoline group; a thiophene group; a dibenzothiophene group; a furan group; a dibenzofuran group; a naphthobenzofuran group; a carbazole group; a benzocarbazole group; a naphthobenzothiophene group; a dibenzosilole group; a naphthobenzosilole group; a hexahydrocarbazole group; a dihydroacridine group; a dihydrodibenzoazasiline group; a phenoxazine group; a phenothiazine group; a dihydrodibenzoazasiline group; a spiro(dibenzosilole-dibenzoazasiline) group; a spiro(acridine-fluorene) group and the like, but are not limited thereto.
In the present specification, the descriptions on the heterocyclic group provided above may be applied to the heteroaryl group except for being aromatic.
In the present specification, the aromatic hydrocarbon ring means a hydrocarbon ring having pi electrons completely conjugated and planar, and the descriptions on the aryl group provided above may be applied thereto except for those that are divalent. The number of carbon atoms of the aromatic hydrocarbon ring may be from 6 to 60; 6 to 30; 6 to 20; or 6 to 10.
In the present specification, the aliphatic hydrocarbon ring has a structure bonding in a ring shape, and means a ring that is not aromatic. Examples of the aliphatic hydrocarbon ring may include cycloalkyl or cycloalkene, and the descriptions on the cycloalkyl group or the cycloalkenyl group may be applied thereto except for those that are divalent. The number of carbon atoms of the aliphatic hydrocarbon ring may be from 3 to 60; 3 to 30; 3 to 20; 3 to 10; 5 to 50; 5 to 30; 5 to 20; 5 to 10; or 5 to 6. In addition, the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring to which an aromatic ring is fused.
In the present specification, the fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring means the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring forming a fused ring. Examples of the fused ring of aromatic and aliphatic may include a 1,2,3,4-tetrahydronaphthalene group, a 2,3-dihydro-1H-indene group and the like, but are not limited thereto.
In the present specification, the “adjacent” group may mean a substituent substituting an atom directly linked to an atom substituted by the corresponding substituent, a substituent sterically most closely positioned to the corresponding substituent, or another substituent substituting an atom substituted by the corresponding substituent. For example, two substituents substituting ortho positions in a benzene ring, and two substituents substituting the same carbon in an aliphatic ring may be interpreted as groups “adjacent” to each other. In addition, substituents linked to consecutive two carbons in the aliphatic ring (total of 4) may also be interpreted as groups “adjacent” to each other.
In the present specification, the meaning of “adjacent groups bonding to each other to form a ring” among the substituents is bonding to adjacent groups to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.
In the present specification, a “5-membered or 6-membered ring formed by adjacent groups bonding to each other” means a ring including substituents participating in the ring formation being 5-membered or 6-membered. It includes an additional ring being fused to the ring including substituents participating in the ring formation.
In the present specification, when substituents of an aromatic hydrocarbon ring or an aryl group bond to adjacent substituents to form an aliphatic hydrocarbon ring, the aliphatic hydrocarbon ring includes two pi electrons (carbon-carbon double bond) of the aromatic hydrocarbon ring or the aryl group even when the double bond is not specified.
In the present specification, the descriptions on the aryl group provided above may be applied to the arylene group except for being a divalent group.
Hereinafter, Chemical Formula 1 will be described in detail.
In Chemical Formula 1,
X1 is O; or S,
Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic heteroring; and a substituted or unsubstituted aliphatic heteroring, or a fused ring of two or more rings selected from the above-described group,
R1 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; an arylalkyl group unsubstituted or substituted with deuterium; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring,
r1 is an integer of 0 to 3, and when r1 is 2 or greater, R1s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1.
In Chemical Formula 1-1,
X1, Cy2 to Cy4, R1 and r1 have the same definitions as in Chemical Formula 1,
R2 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring, and
r2 is an integer of 0 to 4, and when r2 is 2 or greater, R2s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1 is the following Chemical Formula 101 or 102.
In Chemical Formulae 101 and 102,
X1, Cy1 to Cy4, R1 and r1 have the same definitions as in Chemical Formula 1.
In one embodiment of the present specification, Chemical Formula 1-1 is represented by the following Chemical Formulae 101-1 and 102-1.
In Chemical Formulae 101-1 and 102-1,
X1, Cy2 to Cy4, R1, R2, r1 and r2 have the same definitions as in Chemical Formula 1-1.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C60 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C60 aromatic heteroring; and a substituted or unsubstituted C2-C60 aliphatic heteroring, or a fused C9-C60 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C30 aromatic heteroring; and a C2-C30 aliphatic heteroring, or a fused C9-C30 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C20 aromatic heteroring; and a substituted or unsubstituted C2-C20 aliphatic heteroring, or a fused C9-C20 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; a substituted or unsubstituted bicyclooctene ring; a substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; and a substituted or unsubstituted naphthobenzosilole ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; a substituted or unsubstituted bicyclooctene ring; a substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dihydroindene ring; a substituted or unsubstituted dihydroanthracene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; or a substituted or unsubstituted naphthobenzosilole ring.
In one embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; a substituted or unsubstituted bicyclooctene ring; a substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; or a substituted or unsubstituted naphthobenzofuran ring.
In one embodiment of the present specification, Cy1 and Cy2 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; and a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring, or a fused C9-C20 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 is a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; or a substituted or unsubstituted xanthene ring.
In one embodiment of the present specification, Cy1 is a benzene ring unsubstituted or substituted with R2; a naphthalene ring unsubstituted or substituted with R2; a fluorene ring unsubstituted or substituted with R2; a tetrahydronaphthalene ring unsubstituted or substituted with R2; a dibenzofuran ring unsubstituted or substituted with R2; a dibenzothiophene ring unsubstituted or substituted with R2; or a xanthene ring unsubstituted or substituted with R2.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; and a substituted or unsubstituted bicyclooctene ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy2 is a benzene ring unsubstituted or substituted with R3; a cyclohexene ring unsubstituted or substituted with R3; a tetrahydronaphthalene ring unsubstituted or substituted with R3; or a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring unsubstituted or substituted with R3.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C60 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C60 aromatic heteroring; and a substituted or unsubstituted C2-C60 aliphatic heteroring, or a fused C9-C60 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C30 aromatic heteroring; and a substituted or unsubstituted C2-C30 aliphatic heteroring, or a substituted or unsubstituted fused C9-C30 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C20 aromatic heteroring; and a substituted or unsubstituted C2-C20 aliphatic heteroring, or a substituted or unsubstituted fused C9-C20 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; and a substituted or unsubstituted naphthobenzosilole ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; or a substituted or unsubstituted naphthobenzosilole ring.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; or a substituted or unsubstituted naphthobenzofuran ring.
In one embodiment of the present specification, Cy3 is a benzene ring unsubstituted or substituted with R4; a naphthalene ring unsubstituted or substituted with R4; a phenanthrene ring unsubstituted or substituted with R4; a fluorene ring unsubstituted or substituted with R4; a benzofluorene ring unsubstituted or substituted with R4; a tetrahydronaphthalene ring unsubstituted or substituted with R4; a dibenzofuran ring unsubstituted or substituted with R4; a dibenzothiophene ring unsubstituted or substituted with R4; a dibenzosilole ring unsubstituted or substituted with R4; a naphthobenzofuran ring unsubstituted or substituted with R4; a naphthobenzothiophene ring unsubstituted or substituted with R4; or a naphthobenzosilole ring unsubstituted or substituted with R4.
In one embodiment of the present specification, Cy4 is a benzene ring unsubstituted or substituted with R5; a naphthalene ring unsubstituted or substituted with R5; a phenanthrene ring unsubstituted or substituted with R5; a fluorene ring unsubstituted or substituted with R5; a benzofluorene ring unsubstituted or substituted with R5; a tetrahydronaphthalene ring unsubstituted or substituted with R5; a dibenzofuran ring unsubstituted or substituted with R5; a dibenzothiophene ring unsubstituted or substituted with R5; a dibenzosilole ring unsubstituted or substituted with R5; a naphthobenzofuran ring unsubstituted or substituted with R5; a naphthobenzothiophene ring unsubstituted or substituted with R5; or a naphthobenzosilole ring unsubstituted or substituted with R5.
In one embodiment of the present specification, Cy1 to Cy4 are each unsubstituted or substituted with substituents of R2 to R5 to describe later.
In one embodiment of the present specification, Cy1 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; and a substituted or unsubstituted aromatic heteroring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy1 is a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; or a substituted or unsubstituted xanthene ring.
In one embodiment of the present specification, Cy1 is a benzene ring; a naphthalene ring; a fluorene ring; a tetrahydronaphthalene ring; a dibenzofuran ring; a dibenzothiophene ring; or a xanthene ring, and the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a cycloalkyl group, an aryl group, a fused hydrocarbon ring group, a heterocyclic group and an amine group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, Cy1 is a benzene ring; a naphthalene ring; a fluorene ring; a tetrahydronaphthalene ring; a dibenzofuran ring; a dibenzothiophene ring; or a xanthene ring, and the ring is unsubstituted or substituted with deuterium; a methyl group; an isopropyl group; a tert-butyl group; a trimethylsilyl group; a phenylpropyl group unsubstituted or substituted with deuterium; a cyclohexyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group or a trimethylsilyl group; a hexahydrocarbazole group unsubstituted or substituted with a methyl group, a tert-butyl group or a phenyl group; a carbazole group; a diphenylamine group unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, a tert-butyl group or a trimethylsilyl group; or an amine group substituted with a tetrahydronaphthalene group unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, Cy1 is a benzene ring, and the benzene ring is unsubstituted or substituted with deuterium; a methyl group; an isopropyl group; a tert-butyl group; a trimethylsilyl group; a phenylpropyl group unsubstituted or substituted with deuterium; a cyclohexyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group or a trimethylsilyl group; a hexahydrocarbazole group unsubstituted or substituted with a methyl group, a tert-butyl group or a phenyl group; a carbazole group; a diphenylamine group unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, a tert-butyl group or a trimethylsilyl group; or an amine group substituted with a tetrahydronaphthalene group unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, Cy1 is a naphthalene ring; a fluorene ring unsubstituted or substituted with a methyl group; a tetrahydronaphthalene ring unsubstituted or substituted with a methyl group; a dibenzofuran ring unsubstituted or substituted with a tert-butyl group; a dibenzothiophene ring unsubstituted or substituted with a tert-butyl group; or a xanthene ring unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, Cy1 is represented by the following Chemical Formula Cy1-1.
In Chemical Formula Cy1-1,
R2 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring,
r2 is an integer of 0 to 4, and when r2 is 2 or greater, R2s are the same as or different from each other, and
* means a position fused to Chemical Formula 1.
In one embodiment of the present specification, R2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heteroring.
In one embodiment of the present specification, R2 is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R2 is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phenylpropyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted hexahydrocarbazole group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted benzene ring; a substituted or unsubstituted benzofuran ring; a substituted or unsubstituted benzothiophene ring; a substituted or unsubstituted indene ring; or a substituted or unsubstituted benzopyran ring.
In one embodiment of the present specification, R2 is hydrogen; deuterium; a methyl group; a propyl group; a butyl group; a silyl group; a phenylpropyl group; a cyclohexyl group; a phenyl group; a hexahydrocarbazole group; a carbazole group; or an amine group, or bonds to adjacent substituents to form a cyclohexene ring; a benzene ring; a benzofuran ring; a benzothiophene ring; an indene ring; or a benzopyran ring, and the substituent or the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R2 is hydrogen; deuterium; a methyl group unsubstituted or substituted with deuterium; a propyl group unsubstituted or substituted with deuterium; a butyl group unsubstituted or substituted with deuterium; a silyl group unsubstituted or substituted with a methyl group or a phenyl group; a phenylpropyl group unsubstituted or substituted with deuterium; a cyclohexyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a butyl group and a silyl group, or a group linking two or more selected from the above-described group; a hexahydrocarbazole group unsubstituted or substituted with a methyl group, a butyl group or a phenyl group; a carbazole group; a diphenylamine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a methyl group, a butyl group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; or an amine group substituted with a tetrahydronaphthalene group unsubstituted or substituted with a methyl group, or bonds to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with a methyl group; a benzene ring; a benzofuran ring unsubstituted or substituted with a butyl group; a benzothiophene ring unsubstituted or substituted with a butyl group; an indene ring unsubstituted or substituted with a methyl group; or a benzopyran ring unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, R2 is hydrogen; deuterium; a methyl group; an isopropyl group; a tert-butyl group; a trimethylsilyl group; a phenylpropyl group unsubstituted or substituted with deuterium; a cyclohexyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group or a trimethylsilyl group; a hexahydrocarbazole group unsubstituted or substituted with a methyl group, a tert-butyl group or a phenyl group; a carbazole group; a diphenylamine group unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, a tert-butyl group or a trimethylsilyl group; or an amine group substituted with a tetrahydronaphthalene group unsubstituted or substituted with a methyl group, or bonds to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with a methyl group; a benzene ring; a benzofuran ring unsubstituted or substituted with a tert-butyl group; a benzothiophene ring unsubstituted or substituted with a tert-butyl group; an indene ring unsubstituted or substituted with a methyl group; or a benzopyran
ring unsubstituted or substituted with a methyl group, and * means a fused position.
R2 bonding to adjacent substituents to form a ring refers to adjacent two R2s bonding to form a ring.
In one embodiment of the present specification, when R2 bonds to adjacent substituents to form a ring, it is represented by any one of the following structural formulae.
In the structural formulae,
X21 is O; S; or CG201G202,
G21, G201 and G202 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
n21 is 1 or 2, g21 is an integer of 0 to 4, g22 is an integer of 0 to 8, and g23 is an integer of 0 to 6,
when g21, g22 and g23 are each 2 or greater, the two or more G21s are the same as or different from each other, and
* means a position fused to Chemical Formula 1.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a substituted or unsubstituted C1-C30 alkyl group.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a substituted or unsubstituted C1-C20 alkyl group.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a substituted or unsubstituted methyl group.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a methyl group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, G21, G201 and G202 are the same as or different from each other, and are hydrogen; deuterium; or a methyl group.
In one embodiment of the present specification, n21 is 2.
In one embodiment of the present specification, g21 is an integer of 1 to 4.
In one embodiment of the present specification, g22 is an integer of 1 to 4.
In one embodiment of the present specification, g23 is an integer of 1 to 4.
In one embodiment of the present specification, when R2 forms a ring, it is represented by any one of the following structural formulae.
In the structural formulae, substituents have the same definitions as above.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring; and a substituted or unsubstituted aliphatic hydrocarbon ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C60 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C60 aromatic hydrocarbon ring and C5-C60 aliphatic hydrocarbon ring.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C30 aromatic hydrocarbon ring and C5-C30 aliphatic hydrocarbon ring.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C20 aromatic hydrocarbon ring and C5-C30 aliphatic hydrocarbon ring.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; and a substituted or unsubstituted bicyclooctene ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a benzene ring; a naphthalene ring; a fluorene ring; a benzofluorene ring; a cyclohexene ring; a cyclopentene ring; and a bicyclooctene ring, or a fused ring of two or more rings selected from the above-described group, and the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a C1-C10 alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more groups selected from the above-described group.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; and a substituted or unsubstituted bicyclooctene ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy2 is one selected from the group consisting of a benzene ring; a naphthalene ring; a cyclohexene ring; a cyclopentene ring; and a bicyclooctene ring, or a fused ring of two or more rings selected from the above-described group, and the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a C1-C10 alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more groups selected from the above-described group.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted benzene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted tetrahydronaphthalene ring; or a substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring.
In one embodiment of the present specification, Cy2 is a benzene ring; a cyclohexene ring; a tetrahydronaphthalene ring; or a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring, and the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a C1-C10 alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more groups selected from the above-described group.
In one embodiment of the present specification, Cy2 is a benzene ring unsubstituted or substituted with deuterium, a methyl group, CD3, an isopropyl group, a tert-butyl group, an adamantyl group or a phenyl group; a cyclohexene ring unsubstituted or substituted with a methyl group; a tetrahydronaphthalene ring unsubstituted or substituted with deuterium, a methyl group, CD3, an isopropyl group or a tert-butyl group; or a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring unsubstituted or substituted with deuterium, a methyl group, CD3, an isopropyl group or a tert-butyl group.
In one embodiment of the present specification, Cy2 is a benzene ring unsubstituted or substituted with deuterium, a methyl group, CD3, an isopropyl group, a tert-butyl group, an adamantyl group or a phenyl group; a cyclohexene ring unsubstituted or substituted with a methyl group; a tetrahydronaphthalene ring unsubstituted or substituted with deuterium, a methyl group or CD3; or a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring
unsubstituted or substituted with a methyl group, and * means a position fused to Chemical Formula 1.
In one embodiment of the present specification, Cy2 is a benzene ring unsubstituted or substituted with R3; a cyclohexene ring unsubstituted or substituted with R3; a tetrahydronaphthalene ring unsubstituted or substituted with R3; or a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene ring unsubstituted or substituted with R3.
In one embodiment of the present specification, Cy2 is represented by the following Chemical Formula Cy2-1 or Cy2-2.
In Chemical Formulae Cy2-1 and Cy2-2,
R3 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring,
n1 is 1 or 2,
r3 is an integer of 0 to 4, and r301 is an integer of 0 to 8,
when r3 and r301 are each 2 or greater, the two or more R3s are the same as or different from each other, and
* means a position fused to Chemical Formula 1.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C60 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C60 aromatic hydrocarbon ring and C5-C60 aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C30 aromatic hydrocarbon ring and C5-C30 aliphatic hydrocarbon ring. In one embodiment of the present specification, R3 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C2-C20 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C20 aromatic hydrocarbon ring and C5-C20 aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heterocyclic group, or bonds to adjacent substituents to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a C1-C20 alkyl group unsubstituted or substituted with deuterium; a C3-C20 cycloalkyl group unsubstituted or substituted with deuterium; a C6-C20 aryl group unsubstituted or substituted with deuterium; or a C2-C20 heterocyclic group unsubstituted or substituted with deuterium, or bonds to adjacent substituents to form a C6-C20 aromatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group unsubstituted or substituted with deuterium; or a C5-C20 aliphatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted adamantyl group; or a substituted or unsubstituted phenyl group, or bonds to adjacent substituents to form a substituted or unsubstituted cyclohexene ring; or a substituted or unsubstituted bicyclooctene ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted adamantyl group; or a substituted or unsubstituted phenyl group, or bonds to adjacent substituents to form a substituted or unsubstituted cyclohexene ring; or a substituted or unsubstituted bicyclooctene ring.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a methyl group; a propyl group; a butyl group; an adamantyl group; or a phenyl group, or bonds to adjacent substituents to form a cyclohexene ring; or a bicyclooctene ring, and the group or the ring is unsubstituted or substituted with deuterium or an alkyl group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a methyl group unsubstituted or substituted with deuterium; a propyl group unsubstituted or substituted with deuterium; a butyl group unsubstituted or substituted with deuterium; an adamantyl group unsubstituted or substituted with deuterium; or a phenyl group unsubstituted or substituted with deuterium, or bonds to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with deuterium, a methyl group or CD3; or a bicyclooctene ring unsubstituted or substituted with deuterium, a methyl group or CD3.
In one embodiment of the present specification, R3 is hydrogen; deuterium; a methyl group; CD3; an isopropyl group; a tert-butyl group; an adamantyl group; or a phenyl group, or bonds to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with deuterium, a methyl group or CD3; or a bicyclo[2.2.2]oct-2-ene
ring unsubstituted or substituted with a methyl group, and * means a position fused to Chemical Formula Cy2-1 or Cy2-2.
In one embodiment of the present specification, when R3 forms a ring, Cy2-1 is represented by any one of the following structural formulae.
In the structural formulae, * means a position fused to Chemical Formula 1, and the structural formulae are unsubstituted or substituted with deuterium or an alkyl group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, the structural formulae are unsubstituted or substituted with deuterium, a methyl group or CD3.
In one embodiment of the present specification, Cy2-2 is represented by the following structural formula.
In the structural formula, * means a position fused to Chemical Formula 1.
In one embodiment of the present specification, n1 is 2.
In one embodiment of the present specification, r3 is an integer of 0 to 4.
In one embodiment of the present specification, r3 is an integer of 1 to 4.
In one embodiment of the present specification, r301 is an integer of 0 to 8.
In one embodiment of the present specification, r301 is an integer of 1 to 8.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; and a substituted or unsubstituted aromatic heteroring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C60 aliphatic hydrocarbon ring; and a substituted or unsubstituted C2-C60 aromatic heteroring, or a fused C9-C60 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; and a substituted or unsubstituted C2-C30 aromatic heteroring, or a substituted or unsubstituted fused C9-C30 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; and a substituted or unsubstituted C2-C20 aromatic heteroring, or a substituted or unsubstituted fused C9-C20 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; and a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring, or a substituted or unsubstituted fused C9-C20 ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently one selected from the group consisting of a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted cyclohexene ring; a substituted or unsubstituted cyclopentene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; and a substituted or unsubstituted naphthobenzosilole ring, or a fused ring of two or more rings selected from the above-described group.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; or a substituted or unsubstituted naphthobenzosilole ring.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring; a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; or a substituted or unsubstituted naphthobenzofuran ring.
In one embodiment of the present specification, Cy3 is a benzene ring unsubstituted or substituted with R4; a naphthalene ring unsubstituted or substituted with R4; a phenanthrene ring unsubstituted or substituted with R4; a fluorene ring unsubstituted or substituted with R4; a benzofluorene ring unsubstituted or substituted with R4; a tetrahydronaphthalene ring unsubstituted or substituted with R4; a dibenzofuran ring unsubstituted or substituted with R4; a dibenzothiophene ring unsubstituted or substituted with R4; a dibenzosilole ring unsubstituted or substituted with R4; a naphthobenzofuran ring unsubstituted or substituted with R4; a naphthobenzothiophene ring unsubstituted or substituted with R4; or a naphthobenzosilole ring unsubstituted or substituted with R4.
In one embodiment of the present specification, Cy4 is a benzene ring unsubstituted or substituted with R5; a naphthalene ring unsubstituted or substituted with R5; a phenanthrene ring unsubstituted or substituted with R5; a fluorene ring unsubstituted or substituted with R5; a benzofluorene ring unsubstituted or substituted with R5; a tetrahydronaphthalene ring unsubstituted or substituted with R5; a dibenzofuran ring unsubstituted or substituted with R5; a dibenzothiophene ring unsubstituted or substituted with R5; a dibenzosilole ring unsubstituted or substituted with R5; a naphthobenzofuran ring unsubstituted or substituted with R5; a naphthobenzothiophene ring unsubstituted or substituted with R5; or a naphthobenzosilole ring unsubstituted or substituted with R5.
In one embodiment of the present specification, Cy2 to Cy4 are each unsubstituted or substituted with substituents of R3 to R5 to describe later.
In one embodiment of the present specification, descriptions on R5 to provide later may be applied to R4.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently represented by the following Chemical Formula 1-A.
In Chemical Formula 1-A,
a dotted line is a position linked to Chemical Formula 1,
R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring, and
r5 is an integer of 0 to 5, and when r5 is 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C2-C60 ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C2-C20 heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted C2-C20 ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a halogen group; a C1-C20 alkyl group unsubstituted or substituted with deuterium; a C6-C20 arylalkyl group unsubstituted or substituted with deuterium; a C3-C20 cycloalkyl group unsubstituted or substituted with deuterium; a silyl group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group; a C6-C20 aryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; or an amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a silyl group, a C1-C20 alkyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group, or bonds to adjacent substituents to form a C2-C30 ring unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a fluoro group; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenylpropyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted tetrahydronaphthalene group; or a substituted or unsubstituted amine group, or two or more R5s bond to a benzene ring to form a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; a substituted or unsubstituted naphthobenzofuran ring; a substituted or unsubstituted naphthobenzothiophene ring; or a substituted or unsubstituted naphthobenzosilole ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a fluoro group; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenylpropyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted tetrahydronaphthalene group; or a substituted or unsubstituted amine group, or two or more R5s bond to a benzene ring to form a substituted or unsubstituted naphthalene ring; a substituted or unsubstituted phenanthrene ring; a substituted or unsubstituted fluorene ring; a substituted or unsubstituted benzofluorene ring; a substituted or unsubstituted tetrahydronaphthalene ring; a substituted or unsubstituted dibenzofuran ring; a substituted or unsubstituted dibenzothiophene ring; a substituted or unsubstituted dibenzosilole ring; or a substituted or unsubstituted naphthobenzofuran ring.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a fluoro group; a methyl group unsubstituted or substituted with deuterium; a propyl group unsubstituted or substituted with deuterium; a butyl group unsubstituted or substituted with deuterium; a phenylpropyl group unsubstituted or substituted with deuterium; a cyclohexyl group unsubstituted or substituted with deuterium; a silyl group unsubstituted or substituted with a methyl group or a phenyl group; a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, a silyl group, a phenyl group, a biphenyl group, a tetrahydronaphthalene group and a naphthyl group, or a group linking two or more selected from the above-described group; a biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, a silyl group, a phenyl group, a biphenyl group, a tetrahydronaphthalene group and a naphthyl group, or a group linking two or more selected from the above-described group; a naphthyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, a silyl group, a phenyl group, a biphenyl group, a tetrahydronaphthalene group and a naphthyl group, or a group linking two or more selected from the above-described group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; or an amine group unsubstituted or substituted with a tetrahydronaphthalene group or a phenyl group, or two or more R5s bond to a benzene ring to form a naphthalene ring; a phenanthrene ring; a dimethylfluorene ring; a diphenylfluorene ring; a benzofluorene ring; a tetrahydronaphthalene ring; a dibenzofuran ring; a dibenzothiophene ring; a dibenzosilole ring; or a naphthobenzofuran ring, and the ring is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, a silyl group, a phenyl group, a biphenyl group, a tetrahydronaphthalene group and a naphthyl group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R5 is hydrogen; deuterium; a cyano group; a fluoro group; a methyl group; CD3; an isopropyl group; a tert-butyl group; a sec-butyl group; a phenylpropyl group; a cyclohexyl group; a trimethylsilyl group; a triphenylsilyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, CD3, CF3, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group or a naphthyl group; a biphenyl group; a naphthyl group; a tetrahydronaphthalene group substituted with a methyl group; or a diphenylamine group, or two or more R5s bond to a benzene ring to form a naphthalene ring unsubstituted or substituted with a phenyl group; a phenanthrene ring; a dimethylfluorene ring unsubstituted or substituted with a tert-butyl group; a diphenylfluorene ring unsubstituted or substituted with a tert-butyl group; a benzofluorene ring unsubstituted or substituted with a methyl group; a tetrahydronaphthalene ring substituted with a methyl group; a dibenzofuran ring unsubstituted or substituted with a tert-butyl group; a dibenzothiophene ring unsubstituted or substituted with a tert-butyl group; a dibenzosilole ring unsubstituted or substituted with a phenyl group; or a naphthobenzofuran ring. Herein, the tetrahydronaphthalene ring substituted with a methyl group is unsubstituted or substituted with a phenyl group unsubstituted or substituted with deuterium, a methyl group, CD3, CF3, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group or a naphthyl group.
In one embodiment of the present specification, a substituent (R5) that is not hydrogen is linked to an ortho position with respect to the dotted line of Chemical Formula 1-A.
R4 bonding to adjacent substituents to form a ring refers to adjacent two R4s bonding to form a ring.
R5 bonding to adjacent substituents to form a ring refers to adjacent two R5s bonding to form a ring.
In one embodiment of the present specification, Chemical Formula 1-A is represented by any one of the following Chemical Formulae 1-A-1 to 1-A-3.
In Chemical Formulae 1-A-1 to 1-A-3,
a dotted line, R5 and r5 have the same definitions as in Chemical Formula 1-A,
G1 is O; S; NG2; CG2G3; or SiG2G3,
G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to adjacent substituents to form a substituted or unsubstituted ring,
n2 is 1 or 2, and
r51 is an integer of 0 to 7, r52 is an integer of 0 to 11, and when r51 and r52 are each 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, n2 is 2.
In one embodiment of the present specification, G1 is O; S; or CG2G3.
In one embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to adjacent substituents to form a substituted or unsubstituted ring.
In one embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, or bond to adjacent substituents to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.
In one embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a C1-C6 alkyl group unsubstituted or substituted with deuterium; or a C6-C30 aryl group unsubstituted or substituted with deuterium or a C1-C6 alkyl group, or bond to adjacent substituents to form a C6-C20 aromatic hydrocarbon ring.
In one embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a methyl group; or a phenyl group, or bond to each other to form a fluorene ring.
In one embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a methyl group; or a phenyl group.
In one embodiment of the present specification, Chemical Formula 1-A-1 is selected from among the following structures.
In the structures,
a dotted line, R5 and r5 have the same definitions as in Chemical Formula 1-A-1, and
r50 is an integer of 0 to 9, r53 is an integer of 0 to 7, and when r50 and r53 are each 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1-A-2 is selected from among the following structures.
In the structures, a dotted line, G1, R5 and r51 have the same definitions as in Chemical Formula 1-A-2.
In one embodiment of the present specification, Chemical Formula 1-A-3 is selected from among the following structures.
In the structures,
a dotted line and R5 have the same definitions as in Chemical Formula 1-A-3,
r54 is an integer of 0 to 9, and r55 is an integer of 0 to 11, and
when r54 and r55 are each 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1-A-3 is selected from among the following structures.
In the structures,
a dotted line and R5 have the same definitions as in Chemical Formula 1-A-3,
r56 is an integer of 0 to 5, r57 is an integer of 0 to 7, and r58 is an integer of 0 to 7, and
when r56 to r58 are each 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1-A-3 is selected from among the following structure.
In the structures,
a dotted line and R5 have the same definitions as in Chemical Formula 1-A-3,
r54 is an integer of 0 to 9, and r55 is an integer of 0 to 11, and
when r54 and r55 are each 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1-A-3 is selected from among the following structures.
In the structures,
a dotted line and R5 have the same definitions as in Chemical Formula 1-A-3,
r55 is an integer of 0 to 11, and when r55 is 2 or greater, R5s are the same as or different from each other.
In one embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently represented by any one of the following structural formulae.
In the structural formulae,
R5 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonds to adjacent substituents to form a substituted or unsubstituted ring,
G2 and G3 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to adjacent substituents to form a substituted or unsubstituted ring,
r5 is an integer of 0 to 5, r50 is an integer of 0 to 9, r51 is an integer of 0 to 7, r53 is an integer of 0 to 7, r54 is an integer of 0 to 9, and r55 is an integer of 0 to 11,
when r5, r50, r51, and r53 to r55 are each 2 or greater, R5s are the same as or different from each other, and
a dotted line means a position linked to Chemical Formula 1.
In one embodiment of the present specification, at least one of Cy3 and Cy4 is a substituted or unsubstituted tetrahydronaphthalene ring.
In one embodiment of the present specification, at least one of Cy3 and Cy4 is represented by Chemical Formula 1-A-3.
In one embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulae 103 to 106.
In Chemical Formulae 103 to 106,
X1, R1 and r1 have the same definitions as in Chemical Formula 1,
R2 to R5 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; an arylalkyl group unsubstituted or substituted with deuterium; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted ring,
n1 is 1 or 2,
r2 and r3 are each an integer of 0 to 4, r4 and r5 are each an integer of 0 to 5, and r301 is an integer of 0 to 8, and
when r2 to r5 and r301 are each 2 or greater, substituents in the parentheses are the same as or different from each other.
In one embodiment of the present specification, the definitions on R5 described above may be applied to R4.
In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C1-C30 alkylthio group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C6-C60 aryloxy group; a substituted or unsubstituted C6-C60 arylthio group; a substituted or unsubstituted C2-C60 heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C1-C10 alkylthio group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted C2-C30 heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C1-C10 alkylthio group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted C2-C30 heterocyclic group; a substituted or unsubstituted C6-C30 arylamine group; or a substituted or unsubstituted C2-C30 heteroarylamine group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C1-C30 alkylthio group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C6-C60 aryloxy group; a substituted or unsubstituted C6-C60 arylthio group; a substituted or unsubstituted C2-C60 heterocyclic group; or a substituted or unsubstituted amine group.
In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C1-C10 alkylthio group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted C2-C30 heterocyclic group; or a substituted or unsubstituted amine group.
In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C1-C10 alkylthio group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted C2-C30 heterocyclic group; a substituted or unsubstituted C6-C30 arylamine group; or a substituted or unsubstituted C2-C30 heteroarylamine group.
In one embodiment of the present specification, R3 may bond to adjacent substituents to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 may bond to adjacent substituents to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; a substituted or unsubstituted C3-C60 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C60 aromatic hydrocarbon ring and C3-C60 aliphatic hydrocarbon ring.
In one embodiment of the present specification, R3 may bond to adjacent substituents to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C3-C30 aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of C6-C30 aromatic hydrocarbon ring and C3-C30 aliphatic hydrocarbon ring.
In one embodiment of the present specification, R4 and R5 may each bond to adjacent substituents to form a substituted or unsubstituted ring.
In one embodiment of the present specification, R4 and R5 may each bond to adjacent substituents to form a substituted or unsubstituted C2-C60 ring.
In one embodiment of the present specification, R4 and R5 may each bond to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group.
In one embodiment of the present specification, R1 is hydrogen; deuterium; 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 cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted tetrahydronaphthalene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted hexahydrocarbazole group; a substituted or unsubstituted cyclohexene-fused hexahydrocarbazole group; a substituted or unsubstituted phenoxazine group; a substituted or unsubstituted phenothiazine group; a substituted or unsubstituted amine group; a substituted or unsubstituted dihydroacridine group; or a substituted or unsubstituted dihydrodibenzoazasiline group.
In one embodiment of the present specification, R1 is unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, an alkoxy group, a silyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R1 is hydrogen; deuterium; an alkyl group unsubstituted or substituted with deuterium; a cycloalkyl group; an aryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group and an alkyl group, or a group linking two or more selected from the above-described group; a heterocyclic group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a silyl group, an alkyl group and an aryl group, or a group linking two or more selected from the above-described group; or an amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a silyl group, an alkyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R1 is hydrogen; deuterium; a methyl group; a tert-butyl group; a phenyl group unsubstituted or substituted with a cyano group; a diphenylamine group unsubstituted or substituted with a trimethylsilyl group; or a hexahydrocarbazole group unsubstituted or substituted with a methyl group or a tert-butyl group.
In one embodiment of the present specification, R1 is represented by any one of the following Chemical Formulae 1-B-1 to 1-B-4.
In Chemical Formulae 1-B-1 to 1-B-4,
G8 is a direct bond; O; S; CG9G10; or SiG9G10,
R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted ring,
G9 and G10 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to adjacent substituents to form a substituted or unsubstituted ring,
g6 is an integer of 0 to 12, and g7 is an integer of 0 to 8,
when g6 and g7 are each 2 or greater, substituents in the parentheses are the same as or different from each other, and
a dotted line means a position bonding to Chemical Formula 1.
In one embodiment of the present specification, G8 is a direct bond.
In one embodiment of the present specification, G8 is O; or S.
In one embodiment of the present specification, G8 is CG9G10; or SiG9G10.
In one embodiment of the present specification, G9 and G10 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, G9 and G10 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.
In one embodiment of the present specification, G9 and G10 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.
In one embodiment of the present specification, G9 and G10 are the same as or different from each other, and each independently a methyl group; or a phenyl group.
In one embodiment of the present specification, R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bond to adjacent substituents to form a substituted or unsubstituted ring.
In one embodiment of the present specification, R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heterocyclic group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C60 ring.
In one embodiment of the present specification, R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heterocyclic group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C30 ring.
In one embodiment of the present specification, R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heterocyclic group, or bond to adjacent substituents to form a substituted or unsubstituted C2-C20 ring.
In one embodiment of the present specification, R101 to R103 and G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a C1-C30 alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; a C3-C30 cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; a silyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; a C6-C30 aryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; or a C2-C30 heterocyclic group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group, or bond to adjacent substituents to form a C2-C30 ring unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a silyl group, a C6-C20 aryl group and a C9-C20 fused hydrocarbon ring group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R101 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R101 is hydrogen; deuterium; 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 cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted tetrahydronaphthalene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
In one embodiment of the present specification, R101 is hydrogen; deuterium; 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; a cyclohexyl group unsubstituted or substituted with deuterium; an adamantyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a naphthyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a fluorenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a tetrahydronaphthalene group unsubstituted or substituted with deuterium, a methyl group or a butyl group; a dibenzofuran group unsubstituted or substituted with deuterium, a methyl group or a butyl group; or a dibenzothiophene group unsubstituted or substituted with deuterium, a methyl group or a butyl group.
In one embodiment of the present specification, R101 is hydrogen; deuterium; a methyl group; CD3; an ethyl group; an isopropyl group; a tert-butyl group; a cyclohexyl group; an adamantyl group; a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, —OCF3, a trimethylsilyl group, a triphenylsilyl group and a phenyl group, or a group linking two or more selected from the above-described group; a biphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.
In one embodiment of the present specification, R101 is hydrogen; deuterium; a methyl group; CD3; an ethyl group; an isopropyl group; a tert-butyl group; a cyclohexyl group; an adamantyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, a tert-butyl group, —OCF3, a trimethylsilyl group, a triphenylsilyl group or a phenyl group; a biphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a dimethylfluorenyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.
In one embodiment of the present specification, R102 and R103 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R102 and R103 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 naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted tetrahydronaphthalene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
In one embodiment of the present specification, R102 and R103 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a naphthyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a fluorenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a tetrahydronaphthalene group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a dibenzofuran group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; or a dibenzothiophene group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group.
In one embodiment of the present specification, R102 and R103 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a fluoro group, a methyl group, a propyl group, a butyl group, a methoxy group, a silyl group and a phenyl group, or a group linking two or more selected from the above-described group; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.
In one embodiment of the present specification, R102 and R103 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, a cyano group, a fluoro group, a methyl group, CD3, CF3, an isopropyl group, a tert-butyl group, a trimethylsilyl group, a triphenylsilyl group or a phenylpropyl group; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group; a dimethylfluorenyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.
In one embodiment of the present specification, G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group, or bond to adjacent substituents to form a substituted or unsubstituted ring.
In one embodiment of the present specification, G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C30 arylsilyl group; or a substituted or unsubstituted C6-C30 aryl group, or bond to adjacent substituents to form a substituted or unsubstituted C3-C30 aliphatic hydrocarbon ring; or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.
In one embodiment of the present specification, G4 to G7 are the same as or different from each other, and each independently hydrogen; deuterium; a C1-C6 alkyl group unsubstituted or substituted with deuterium; a C1-C18 alkylsilyl group; a C6-C60 arylsilyl group; or a C6-C30 aryl group unsubstituted or substituted with deuterium or a C1-C6 alkyl group, or bond to adjacent substituents to form a C3-C20 aliphatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group; or a C6-C20 aromatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group.
In one embodiment of the present specification, G4 and G5 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, G4 and G5 are a methyl group.
In one embodiment of the present specification, G6 and G7 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted trimethylsilyl group; or a substituted or unsubstituted phenyl group, or bond to adjacent substituents to form a substituted or unsubstituted cyclohexene ring; or a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, G6 and G7 are the same as or different from each other, and each independently hydrogen; deuterium; a methyl group; a tert-butyl group; a trimethylsilyl group; or a phenyl group, or bond to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, G6 is hydrogen; deuterium; a methyl group; a tert-butyl group; a trimethylsilyl group; or a phenyl group, or bonds to adjacent substituents to form a cyclohexene ring unsubstituted or substituted with a methyl group.
In one embodiment of the present specification, G7 is hydrogen; or deuterium.
In one embodiment of the present specification, G7 is hydrogen.
In one embodiment of the present specification, Chemical Formula 1-B-3 is represented by any one of the following structural formulae.
In the structural formulae,
a dotted line, G6 and g6 have the same definitions as in Chemical Formula 2, and
g6′ is an integer of 0 to 10, and when g6′ is 2 or greater, the two or more G6s are the same as or different from each other.
In one embodiment of the present specification, Chemical Formula 1-B-4 is represented by any one of the following structural formulae.
In the structural formulae, a dotted line, G7, G9, G10 and g7 have the same definitions as in Chemical Formula 1-B-4.
In one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; an alkyl group unsubstituted or substituted with deuterium; an arylalkyl group unsubstituted or substituted with deuterium; a cycloalkyl group unsubstituted or substituted with deuterium; a silyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, an alkyl group and an aryl group, or a group linking two or more selected from the above-described group; an aryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a silyl group, an alkyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group; a heterocyclic group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a silyl group, an alkyl group and an aryl group, or a group linking two or more selected from the above-described group; or an amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, a silyl group, an alkyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group, or bond to adjacent substituents to form a ring unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, an aryl group and a fused hydrocarbon ring group, or a group linking two or more selected from the above-described group, and
the number of carbon atoms of the alkyl group is from 1 to 20, the number of carbon atoms of the arylalkyl group is from 7 to 50, the number of carbon atoms of the cycloalkyl group is from 3 to 30, the number of carbon atoms of the aryl group is from 6 to 30, the number of carbon atoms of the fused hydrocarbon ring group is from 9 to 30, the number of carbon atoms of the heterocyclic group is from 2 to 30, and the heteroring includes one or more of N, O, S and Si as a heteroatom.
In one embodiment of the present specification, in Chemical Formula 1, at least one of Cy1 to Cy4 and R1 includes a ring to which a substituted or unsubstituted aliphatic hydrocarbon ring is fused.
In one embodiment of the present specification, in Chemical Formula 1, at least one of Cy1 to Cy4 and R1 includes a ring to which a C5-C30 aliphatic hydrocarbon ring unsubstituted or substituted with a C1-C20 alkyl group is fused.
In one embodiment of the present specification, the aliphatic hydrocarbon ring may include a hexagonal ring or a pentagonal ring.
In one embodiment of the present specification, in Chemical Formula 1, at least one of Cy1 to Cy4 and R1 includes a ring to which a substituted or unsubstituted cyclohexene ring; or a substituted or unsubstituted bicyclooctene ring is fused.
In one embodiment of the present specification, in Chemical Formula 1, at least one of Cy1 to Cy4 and R1 includes a ring to which a cyclohexene ring unsubstituted or substituted with a methyl group; or a bicyclooctene ring unsubstituted or substituted with a methyl group is fused.
In one embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulae 107 to 109.
In Chemical Formulae 107 to 109,
substituents have the same definitions as above, and r3′ is an integer of 0 to 10.
In one embodiment of the present specification, Chemical Formula 1 is one selected from among the following compounds.
Hereinafter, Chemical Formula 2 will be described in detail.
In Chemical Formula 2,
L1 and L2 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,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R11 to R13 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted ring, and
r11 is an integer of 0 to 8, r12 and r13 are each an integer of 0 to 4, and when r11 to r13 are each 2 or greater, substituents in the parentheses are the same as or different from each other.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heterocyclic group.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heterocyclic group.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C2-C20 N-containing heterocyclic group; a substituted or unsubstituted C2-C20 O-containing heterocyclic group; or a substituted or unsubstituted C2-C20 S-containing heterocyclic group.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a C6-C30 aryl group unsubstituted or substituted with deuterium, a C1-C20 alkyl group or a C6-C30 aryl group; or a C2-C30 heterocyclic group unsubstituted or substituted with deuterium, a C1-C20 alkyl group or a C6-C30 aryl group.
In one embodiment of the present specification, Ar1 and Ar2 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 quaterphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; a phenyl group substituted with a naphthyl group; a biphenyl group; a terphenyl group; a quaterphenyl group; a naphthyl group; a naphthyl group substituted with a phenyl group; a phenanthrenyl group; a triphenylenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a dibenzofuran group; a dibenzothiophene group; or a carbazole group, and Ar1 and Ar2 are unsubstituted or substituted with deuterium.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently one selected from among the following structures.
In the structures,
the structures are unsubstituted or substituted with deuterium,
a dotted line is a position linked to Chemical Formula 2, and
R14 and R15 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.
In one embodiment of the present specification, R14 and R15 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.
In one embodiment of the present specification, R14 and R15 are the same as or different from each other, and each independently a methyl group; or a phenyl group.
In one embodiment of the present specification, L1 and L2 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.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 divalent heterocyclic group.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 divalent heterocyclic group.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 divalent heterocyclic group.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent carbazole group.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a C6-C30 arylene group unsubstituted or substituted with deuterium.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or selected from among the following structures.
In the structures,
the structures are unsubstituted or substituted with deuterium,
a dotted line is a position linked to Chemical Formula 2, and
R14 and R15 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.
In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or selected from among the following structures.
In the structures,
a dotted line is a position linked to Chemical Formula 2, and
R14 and R15 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.
In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C1-C10 alkylthio group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted C2-C30 heterocyclic group; or a substituted or unsubstituted amine group, or bond to adjacent substituents to form a substituted or unsubstituted C3-C30 ring.
In one embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; or deuterium.
In one embodiment of the present specification, R11 to R13 are hydrogen.
In one embodiment of the present specification, -L1-Ar1 and -L2-Ar2 of Chemical Formula 2 are the same as each other.
In one embodiment of the present specification, -L1-Ar1 and -L2-Ar2 of Chemical Formula 2 are different from each other.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; or a heterocyclic group unsubstituted or substituted with deuterium, an alkyl group or an aryl group,
L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group unsubstituted or substituted with deuterium,
R11 to R13 are the same as or different from each other, and each independently hydrogen; or deuterium, and
the number of carbon atoms of the alkyl group is from 1 to 20, the number of carbon atoms of the aryl group and the arylene group is from 6 to 30, the number of carbon atoms of the heterocyclic group is from 2 to 30, and the heterocyclic group includes one or more of N, O, S and Si as a heteroatom.
In one embodiment of the present specification, Chemical Formula 2 is the following Chemical Formula 201.
In Chemical Formula 201,
L1, L2, Ar1 and Ar2 have the same definitions as in Chemical Formula 2.
In one embodiment of the present specification, Chemical Formula 2 is one selected from among the following compounds.
The substituents of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 may bond using methods known in the art, and types, positions and the number of the substituents may vary depending on technologies known in the art. For example, the compound may be synthesized using methods such as synthesis examples to describe later.
A conjugation length of the compound and the energy band gap are closely related. Specifically, the energy band gap decreases as the conjugation length of the compound increases.
In the present disclosure, compounds having various energy band gaps may be synthesized by introducing various substituents to the core structure as above. In addition, HOMO and LUMO energy levels of the compound may also be adjusted in the present disclosure by introducing various substituents to the core structure having a structure as above.
In addition, by introducing various substituents to the core structure having a structure as above, compounds having unique properties of the introduced substituents may be synthesized. For example, by introducing substituents normally used as hole injection layer materials, hole transfer layer materials, light emitting layer materials and electron transfer layer materials used when manufacturing an organic light emitting device to the core structure, materials satisfying conditions required for each organic material layer may be synthesized.
In addition, an organic light emitting device according to the present disclosure includes an anode; a cathode; and an organic material layer provided between the anode and the cathode, wherein the organic material layer includes a light emitting layer and a first organic material layer, the first organic material layer is provided between the anode and the light emitting layer, the light emitting layer includes the compound of Chemical Formula 1, and the first organic material layer includes the compound of Chemical Formula 2.
The organic light emitting device of the present disclosure may be manufactured using common organic light emitting device manufacturing methods and materials except that one or more organic material layers are formed using the compound described above.
The compound may be formed to an organic material layer using a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, a spray method, roll coating and the like, but is not limited thereto.
The organic material layer of the organic light emitting device of the present disclosure may be formed in a single layer structure, but may be formed in a multilayer structure in which two or more organic material layers are laminated. For example, the organic light emitting device of the present disclosure may have a structure including a hole injection layer, a hole transfer layer, a layer carrying out hole injection and hole transfer at the same time, a light emitting layer, an electron transfer layer, an electron injection layer and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers or a larger number of organic material layers.
In one embodiment of the present specification, the first organic material layer is provided between the light emitting layer and the anode. In other words, the first organic material layer is included in a hole transfer area.
In one embodiment of the present specification, the first organic material layer is provided to be in direct contact with the light emitting layer. Herein, additional organic material layers are not included between the light emitting layer and the first organic material layer.
In one embodiment of the present specification, the first organic material layer is provided between the light emitting layer and the anode, and is provided to be in direct contact with the light emitting layer.
In one embodiment of the present specification, the first organic material layer is a hole injection layer, a hole transfer layer or an electron blocking layer.
In one embodiment of the present specification, the first organic material layer is a hole transfer layer adjacent to the light emitting layer.
In one embodiment of the present specification, the first organic material layer is an electron blocking layer.
In one embodiment of the present specification, the first organic material layer is an electron blocking layer, and a hole transfer layer or a hole injection layer is provided between the anode and the first organic material layer. Herein, the hole transfer layer or the hole injection layer may include an arylamine-based compound, and may further include a P-dopant.
In one embodiment of the present specification, the light emitting layer has a maximum emission peak present in a range of 400 nm to 500 nm. In other words, the light emitting layer is a blue light emitting layer.
In one embodiment of the present specification, the light emitting layer includes the compound of Chemical Formula 1 as a dopant.
In one embodiment of the present specification, the light emitting layer includes the polycyclic compound of Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.
In one embodiment of the present specification, the light emitting layer includes an anthracene-based compound as a host.
In one embodiment of the present specification, the light emitting layer includes a host and a dopant, and includes the host and the dopant in a weight ratio of 99:1 to 1:99, preferably in a weight ratio of 99:1 to 70:30, and more preferably in a weight ratio of 99:1 to 90:10.
The organic light emitting device according to one embodiment of the present specification may include an additional light emitting layer in addition to the light emitting layer including the compound of Chemical Formula 1. Herein, the additional light emitting layer includes a phosphorescent dopant or a fluorescent dopant, and includes a phosphorescent host or a fluorescent host. The additional light emitting layer emits red, green or blue light.
According to one embodiment of the present specification, the light emitting layer includes one or more types of hosts.
According to one embodiment of the present specification, the light emitting layer includes two or more types of mixed hosts.
In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers and a cathode are consecutively laminated on a substrate (normal type).
In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure in a reverse direction in which a cathode, one or more organic material layers and an anode are consecutively laminated on a substrate (inverted type).
The organic light emitting device of the present specification may have structures as illustrated in
According to one embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may have a form in which each organic light emitting device is joined by a charge generating layer. A device having a tandem structure may be driven at a lower current compared to a unit device based on the same brightness, and thereby has an advantage of significantly enhancing lifetime properties of the device.
According to one embodiment of the present specification, the organic material layer includes a first stack including one or more light emitting layers; a second stack including one or more light emitting layers; and one or more charge generating layers provided between the first stack and the second stack.
According to another embodiment of the present specification, the organic material layer includes a first stack including one or more light emitting layers; a second stack including one or more light emitting layers; and a third stack including one or more light emitting layers, and one or more charge generating layers each provided between the first stack and the second stack; and between the second stack and the third stack.
In the present specification, the charge generating layer means a layer generating holes and electrons when applying a voltage. The charge generating layer may be an N-type charge generating layer or a P-type charge generating layer. In the present specification, the N-type charge generating layer means a charge generating layer locating closer to an anode than the P-type charge generating layer, and the P-type charge generating layer means a charge generating layer locating closer to a cathode than the N-type charge generating layer.
The N-type charge generating layer and the P-type charge generating layer may be provided to be in contact with each other, and an NP junction is formed in this case. By the NP junction, holes are readily formed in the P-type charge generating layer, and electrons are readily formed in the N-type charge generating layer. The electrons are transferred in an anode direction through a LUMO level of the N-type charge generating layer, and the holes are transferred in a cathode direction through a HOMO level of the P-type organic material layer.
The first stack, the second stack and the third stack each include one or more light emitting layers, and may further include one or more layers of a hole injection layer, a hole transfer layer, an electron blocking layer, an electron injection layer, an electron transfer layer, a hole blocking layer, a layer carrying out hole transfer and hole injection at the same time (hole injection and transfer layer), and a layer carrying out electron transfer and electron injection at the same time (electron injection and transfer layer).
The organic light emitting device including the first stack and the second stack is illustrated in
The organic light emitting device including the first stack to the third stack is illustrated in
The N-type charge generating layer may be 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, a hexaazatriphenylene derivative or the like, but is not limited thereto. In one embodiment, the N-type charge generating layer may include a benzimidazophenanthridine-based derivative and a metal of Li at the same time.
The P-type charge generating layer may include an arylamine-based derivative and a compound including a cyano group at the same time.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art except that the organic material layer includes the compound.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed with materials the same as or different from each other.
For example, the organic light emitting device according to the present disclosure may be manufactured by forming an anode on a substrate by depositing a metal, a metal oxide having conductivity, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, forming an organic material layer including one or more layers selected from the group consisting of a hole injection layer, a hole transfer layer, a layer carrying out hole transfer and hole injection at the same time, a light emitting layer, an electron transfer layer, an electron injection layer, and a layer carrying out electron transfer and electron injection at the same time, and then depositing a material usable as a cathode thereon. In addition to such a method, the organic light emitting device may also be manufactured by consecutively depositing a cathode material, an organic material layer and an anode material on a substrate.
The organic material layer may have a multilayer structure including a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer and the like, but is not limited thereto, and may have a single layer structure. In addition, using various polymer materials, the organic material layer may be prepared to a smaller number of layers using a solvent process instead of a deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, a thermal transfer method or the like.
The anode is an electrode that injects holes, and as the anode material, materials having large work function are normally preferred so that hole injection to an organic material layer is smooth. Specific examples of the anode material usable in the present disclosure include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
The cathode is an electrode that injects electrons, and as the cathode material, materials having small work function are normally preferred so that electron injection to an organic material layer is smooth. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF/Al or LiO2/Al, and the like, but are not limited thereto.
The hole injection layer is a layer performing a role of smoothly injecting holes from an anode to a light emitting layer, and may have a single layer or multilayer structure. The hole injection material is a material capable of favorably receiving holes from an anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably in between the work function of the anode material and the HOMO of surrounding organic material layers. Specific examples of the hole injection material include metal porphyrins, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline- and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. The hole injection layer having a thickness of 1 nm or greater has an advantage of preventing hole injection properties from declining, and the thickness being 150 nm or less has an advantage of preventing a driving voltage from increasing to enhance hole migration caused by the hole injection layer being too thick. In one embodiment of the present specification, the hole injection layer has a multilayer structure of two or more layers.
The hole transfer layer may perform a role of smoothly transferring holes. As the hole transfer material, materials capable of receiving holes from an anode or a hole injection layer, moving the holes to a light emitting layer, and having high mobility for the holes are suited. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having conjugated parts and non-conjugated parts together, and the like, but are not limited thereto.
A hole buffer layer may be further provided between the hole injection layer and the hole transfer layer, and may include hole injection or transfer materials known in the art.
An electron blocking layer may be provided between the hole transfer layer and the light emitting layer. As the electron blocking layer, the spiro compound described above, or materials known in the art may be used.
The light emitting layer may emit red, green or blue, and may be formed with a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in a visible region by receiving holes and electrons from a hole transfer layer and an electron transfer layer, respectively, and binding the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-, benzothiazole- and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
As the host material of the light emitting layer, fused aromatic ring derivatives, heteroring-containing compounds or the like may be included. Specifically, anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds or the like may be included as the fused aromatic ring derivative, and carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives or the like may be included as the heteroring-containing compound, however, the host material is not limited thereto.
When the light emitting layer emits red light, phosphorescent materials such as bis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) or octaethylporphyrin platinum (PtOEP), or fluorescent materials such as tris(8-hydroxyquinolino)aluminum (Alq3) may be used as the light emitting dopant, however, the light emitting dopant is not limited thereto. When the light emitting layer emits green light, phosphorescent materials such as fac tris(2-phenylpyridine)iridium (Ir(ppy)3), or fluorescent materials such as tris(8-hydroxyquinolino)aluminum (Alq3) may be used as the light emitting dopant, however, the light emitting dopant is not limited thereto. When the light emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers or PPV-based polymers may be used as the light emitting dopant, however, the light emitting dopant is not limited thereto.
A hole blocking layer may be provided between the electron transfer layer and the light emitting layer, and materials known in the art may be used.
The electron transfer layer may perform a role of smoothly transferring electrons, and may have a single layer or multilayer structure. As the electron transfer material, materials capable of favorably receiving electrons from a cathode, moving the electrons to a light emitting layer, and having high mobility for the electrons are suited. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes including Alg3; organic radical compounds; hydroxyflavon-metal complexes, and the like, but are not limited thereto. The electron transfer layer may have a thickness of 1 nm to 50 nm. The electron transfer layer having a thickness of 1 nm or greater has an advantage of preventing electron transfer properties from declining, and the thickness being 50 nm or less has an advantage of preventing a driving voltage from increasing to enhance electron migration caused by the electron transfer layer being too thick. In one embodiment of the present specification, the electron transfer layer has a multilayer structure of two or more layers, and the electron transfer layer adjacent to the cathode includes an n-type dopant.
The electron injection layer may perform a role of smoothly injecting electrons. As the electron injection material, compounds having an electron transferring ability, having an electron injection effect from a cathode, having an excellent electron injection effect for a light emitting layer or light emitting material, and preventing excitons generated in the light emitting layer from moving to a hole injection layer, and in addition thereto, having an excellent thin film forming ability are preferred. Specific examples thereof may include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone or the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
The metal complex compound includes 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato)gallium and the like, but is not limited thereto.
The hole blocking layer is a layer blocking holes from reaching a cathode, and may be generally formed under the same condition as the hole injection layer. Specific examples thereof may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like, but are not limited thereto.
The organic light emitting device according to the present disclosure may be a top-emission type, a bottom-emission type or a dual-emission type depending on the materials used.
Hereinafter, the present specification will be described in detail with reference to examples, comparative examples and the like. However, the examples and the comparative examples according to the present specification may be modified to various other forms, and the scope of the present specification is not to be construed as being limited to the examples and the comparative examples described below. The examples and the comparative examples of the present specification are provided in order to more fully describe the present specification to those having average knowledge in the art.
After dissolving 1-bromo-3-chloro-5-methylbenzene (146 mmol, 30 g, 1 eq.) and bis(4-(tertbutyl)phenyl)amine (146 mmol, 41.1 g, 1 eq.) in toluene (0.2 M, 730 ml) in a 3-neck flask, sodium tertbutoxide (219 mmol, 21 g, 1.5 eq.) and bis(tri-tert-butylphosphine)palladium(0) (1.46 mmol, 0.75 g, 0.01 eq.) were introduced thereto, and the result was stirred for 1 hour under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then distilled water was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound A-2-1 (49 g, yield 83%, MS[M+H]+=405).
After dissolving 5-tertbutyl-[1,1′-biphenyl]-2-amine (66.6 mmol, 15 g, 1 eq.) and 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene (66.6 mmol, 21.5 g, 1 eq.) in toluene (0.2 M, 335 ml) in a 3-neck flask, sodium tertbutoxide (99.9 mmol, 9.60 g, 1.5 eq.) and bis(tri-tert-butylphosphine)palladium(0) (0.666 mmol, 0.340 g, 0.01 eq.) were introduced thereto, and the result was stirred for 12 hours under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then H2O was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound A-2-2 (24.2 g, yield 78%, MS[M+H]+=468).
After dissolving Compound A-2-1 (49.3 mmol, 20 g, 1 eq.) and Compound A-2-2 (49.3 mmol, 23.0 g, 1 eq.) in toluene (0.2 M, 250 ml) in a 3-neck flask, sodium tert-butoxide (73.9 mmol, 7.10 g, 1.5 eq.) and bis(tri-tertbutylphosphine)palladium(0) (0.493 mmol, 0.252 g, 0.01 eq.) were introduced thereto, and the result was stirred for 12 hours under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then H2O was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound A-2-3 (36.1 g, yield 88%, MS[M+H]+=837).
After dissolving Compound A-2-3 (43.1 mmol, 36.1 g, 1 eq.) in 1,2-dichlorobenzene (0.1 M, 430 ml) in a 3-neck flask, boron triiodide (69.0 mmol, 27.0 g, 1.6 eq.) was introduced thereto, and the result was stirred for 3 hours at 140° C. under the argon atmosphere. The reaction material was cooled to 0° C., and after adding N,N-diisopropylethylamine (388 mmol, 50.2 g, 9 eq.) thereto, the result was stirred for 1 hour. The result was extracted in a separatory funnel using toluene and H2O. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography and then went through sublimation purification to obtain Compound A-2 (7.1 g, yield 19%, MS[M+H]+=603).
Compound A-1-1 (50.4 g, yield 74%, MS[M+H]+=448) was obtained in the same manner as in Synthesis Example 1 except that Compound S-8 (1 eq.) was used instead of Compound S-1.
After dissolving Compound A-1-1 (29.4 g, 49.6 mmol, 1 eq.), 4-(tert-butyl)aniline (7.78 g, 52.1 mmol, 1.05 eq.), Pd(tBu3P)2 (0.25 g, 0.01 eq.) and NaOt-Bu (7.2 g, 1.5 eq.) in toluene (250 ml), the result was stirred under reflux. When the reaction was finished, the result was cooled to room temperature, and then the reaction material was transferred to a separatory funnel and extracted. The result was dried with MgSO4, filtered and concentrated, and the next reaction proceeded without further purification.
After dissolving Compound S-10 (11.1 g, 51.1 mmol, 1.5 eq.), Pd(tBu3P)2 (0.25 g, 0.1 eq.) and NaOt-Bu (7.2 g, 1.5 eq.) in toluene (204 ml), the result was stirred under reflux. When the reaction was finished, the result was cooled to room temperature, and then the reaction material was transferred to a separatory funnel and extracted. The result was dried with MgSO4, filtered and concentrated, and purified using column chromatography to obtain Compound A-1-2 (22.9 g, 55%).
MS:[M+H]+=749
Compound A-1 (2.8 g, yield 17%, MS[M+H]+=757) was obtained in the same manner as in Synthesis Example 4 except that Compound A-1-2 (16.5 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-7-1 (14.6 g, yield 62%, MS[M+H]+=538) was obtained in the same manner as in Synthesis Example 2 except that Compounds S-6 (13 g, 1 eq.) and S-7 were used instead of Compounds S-3 and S-4.
Compound A-7-2 (16.5 g, yield 74%, MS[M+H]+=907) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-2-1 (10 g, 1 eq.) and A-7-1 were used instead of Compounds A-2-1 and A-2-2.
Compound A-7 (2.8 g, yield 17%, MS[M+H]+=915) was obtained in the same manner as in Synthesis Example 4 except that Compound A-7-2 (16.5 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-3-1 (17.9 g, yield 68%, MS[M+H]+=536) was obtained in the same manner as in Synthesis Example 1 except that Compound 5-11 (20.3 g, 1 eq.) was used instead of Compound S-2.
Compound A-3-2 (9.6 g, yield 57%, MS[M+H]+=838) was obtained in the same manner as in Synthesis Example 6 except that Compound A-3-1 (1 eq.) was used instead of Compound A-1-1.
Compound A-3 (3.1 g, yield 22%, MS[M+H]+=846) was obtained in the same manner as in Synthesis Example 4 except that Compound A-3-2 (1 eq.) was used instead of Compound A-2-3.
Compound A-4-1 (17.9 g, yield 68%, MS[M+H]+=541) was obtained in the same manner as in Synthesis Example 1 except that Compound S-12 (20.3 g, 1 eq.) was used instead of Compound S-2.
Compound A-4-2 (15.5 g, yield 59%, MS[M+H]+=392) was obtained in the same manner as in Synthesis Example 2 except that Compound S-9 (10 g, 1 eq.) was used instead of Compound S-3.
Compound A-4-3 (18.8 g, yield 71%, MS[M+H]+=857) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-4-1 (16 g, 1 eq.) and A-4-2 (11.6 g, 1 eq.) were used instead of Compounds A-2-1 and A-2-2.
Compound A-4 (4.2 g, yield 23%, MS[M+H]+=905) was obtained in the same manner as in Synthesis Example 4 except that Compound A-4-3 (18 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-5-1 (18.5 g, yield 77%, MS[M+H]+=494) was obtained in the same manner as in Synthesis Example 1 except that Compound S-13 (18 g, 1 eq.) was used instead of Compound S-2.
Compound A-5-2 (9.9 g, yield 64%, MS[M+H]+=849) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-5-1 (9 g, 1 eq.) and A-4-2 (7.1 g, 1 eq.) were used instead of Compounds A-2-1 and A-2-2.
Compound A-5 (3.5 g, yield 35%, MS[M+H]+=857) was obtained in the same manner as in Synthesis Example 4 except that Compound A-5-2 (9.9 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-6-1 (124.1 g, yield 84%, MS[M+H]+=590) was obtained in the same manner as in Synthesis Example 1 except that Compound S-14 (22.7 g, 1 eq.) was used instead of Compound S-2.
Compound A-6-2 (8.8 g, yield 55%, MS[M+H]+=299) was obtained in the same manner as in Synthesis Example 2 except that Compounds S-9 (8 g, 1 eq.) and S-15 (12.3 g) were used instead of Compounds S-3 and S-4.
Compound A-6-3 (10.6 g, yield 61%, MS[M+H]+=523) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-6-1 (12 g, 1 eq.) and A-6-2 (6.1 g) were used instead of Compounds A-2-1 and A-2-2.
Compound A-6 (2.5 g, yield 26%, MS[M+H]+=861) was obtained in the same manner as in Synthesis Example 4 except that Compound A-6-3 (9.5 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-11-1 (18.0 g, yield 77%, MS[M+H]+=601) was obtained in the same manner as in Synthesis Example 1 except that Compound S-16 (18.6 g, 1 eq.) was used instead of Compound S-2.
Compound A-11-2 (12.5 g, yield 71%, MS[M+H]+=446) was obtained in the same manner as in Synthesis Example 2 except that Compounds S-17 (8 g, 1 eq.) was used instead of Compound S-3.
Compound A-11-3 (18.5 g, yield 71%, MS[M+H]+=1010) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-11-1 (15.5 g, 1 eq.) and A-11-2 (11.5 g) were used instead of Compounds A-2-1 and A-2-2.
Compound A-11 (3.2 g, yield 22%, MS[M+H]+=1017) was obtained in the same manner as in Synthesis Example 4 except that Compound A-11-3 (14.5 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-8-1 (16.5 g, yield 66%, MS[M+H]+=494) was obtained in the same manner as in Synthesis Example 1 except that Compound S-18 (1 eq.) was used instead of Compound S-2.
Compound A-8-2 (9.1 g, yield 62%, MS[M+H]+=850) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-8-1 (1 eq.) and A-4-2 were used instead of Compounds A-2-1 and A-2-2.
Compound A-8 (3.4 g, yield 27%, MS[M+H]+=858) was obtained in the same manner as in Synthesis Example 4 except that Compound A-8-2 (1 eq.) was used instead of Compound A-2-3.
Compound A-9-1 (35.5 g, yield 79%, MS[M+H]+=556) was obtained in the same manner as in Synthesis Example 1 except that Compounds S-8 (20 g, 1 eq.) and S-19 (31.5 g) were used instead of Compounds S-1 and S-2.
Compound A-9-2 (11.8 g, yield 68%, MS[M+H]+=966) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-9-1 (10 g, 1 eq.) and A-11-2 (8 g) were used instead of Compounds A-2-1 and A-2-2.
Compound A-9 (3.9 g, yield 39%, MS[M+H]+=973) was obtained in the same manner as in Synthesis Example 4 except that Compound A-9-2 (10 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-10-1 (19.9 g, yield 68%, MS[M+H]+=598) was obtained in the same manner as in Synthesis Example 1 except that Compounds S-20 (1 eq.) and S-11 (20.3 g, 1 eq.) were used instead of Compounds S-1 and S-2.
Compound A-10-2 (9.1 g, yield 57%, MS[M+H]+=843) was obtained in the same manner as in Synthesis Example 6 except that Compounds A-10-1 (1 eq.) and S-21 were used instead of Compounds A-1-1 and 5-10.
Compound A-10 (1.9 g, yield 12%, MS[M+H]+=851) was obtained in the same manner as in Synthesis Example 4 except that Compound A-10-2 (1 eq.) was used instead of Compound A-2-3.
Compound A-12-1 (21.1 g, yield 67%, MS[M+H]+=571) was obtained in the same manner as in Synthesis Example 1 except that Compound S-22 (1 eq.) was used instead of Compound S-2.
Compound A-12-2 (10.2 g, yield 53%, MS[M+H]+=927) was obtained in the same manner as in Synthesis Example 6 except that Compounds A-12-1 (1 eq.) was used instead of Compound A-1-1, and Compound S-17 was used instead of compound S-9.
Compound A-12 (1.7 g, yield 15%, MS[M+H]+=935) was obtained in the same manner as in Synthesis Example 4 except that Compound A-12-2 (1 eq.) was used instead of Compound A-2-3.
Compound A-13-1 (24 g, yield 68%, MS[M+H]+=625) was obtained in the same manner as in Synthesis Example 1 except that Compound S-23 (1 eq.) was used instead of Compound S-2.
Compound A-13-2 (18.1 g, yield 69%, MS[M+H]+=1035) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-13-1 (1 eq.) and A-11-2 (1 eq.) were used instead of Compounds A-2-1 and A-2-2.
Compound A-13 (3.3 g, yield 24%, MS[M+H]+=1043) was obtained in the same manner as in Synthesis Example 4 except that Compound A-13-2 (1 eq.) was used instead of Compound A-2-3.
Preparation was conducted in the same manner as in Synthesis Example 1 except that Compounds S-24 (20 g, 1 eq.) and S-2 (27.1 g) were used instead of Compounds S-1 and S-2, and the next reaction proceeded without further purification.
After dissolving the reaction product that did not go through purification in tetrahydrofuran (THF) (240 mL), potassium carbonate (17.3 g, 1.3 eq.) dissolved in water (80 mL) was slowly added thereto. Perfluorobutanesulfonyl fluoride 43.7 g (1.5 eq.) was added thereto, and the result was stirred for 2 hours at room temperature. When the reaction was completed, the reaction solution was separated by water and ethyl acetate thereto, and then filtered after treating with MgSO4 (anhydrous). The filtered solution was removed by distillation under vacuum, and purified using a column chromatography method to obtain Compound A-14-1 (44.7 g, yield 67%).
A flask holding Compound A-14-1 (12 g, 17.4 mmol, 1 eq.), Compound A-4-2 (7.2 g, 1.05 eq.), palladium(0) bis(dibenzylideneacetone) (Pd(dba)2) (0.1 g, 0.01 eq.), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (0.17 g, 0.02 eq.), Cs2CO3 (17 g, 3 eq.) and xylene (90 ml) was heated to 140° C., and the mixture was stirred for 12 hours. The reaction solution was cooled to room temperature, separated by adding sat. aq. NH4Cl and toluene thereto, and the solvent was removed by distillation under vacuum. The result was purified using silica gel column chromatography (ethyl acetate/hexane) to obtain Compound A-14-2 (9.8 g, yield 72%, MS[M+H]+=781).
Compound A-14-3 (4.0 g, yield 42%, MS[M+H]+=775) was obtained in the same manner as in Synthesis Example 4 except that Compound A-14-2 (9.7 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-14 (3.8 g, yield 74%, MS[M+H]+=995) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-14-3 (4 g, 1 eq.) and S-25 (1.5 g, 1.2 eq.) were used instead of Compounds A-2-1 and A-2-2.
Compound A-15-1 (38.2 g, yield 65%) was obtained in the same manner as in Synthesis Example 40 except that Compound S-19 (1 eq.) was used instead of Compound S-2.
Compound A-15-2 (17.6 g, yield 55%, MS[M+H]+=944) was obtained in the same manner as in Synthesis Example 41 except that Compounds A-15-1 (1 eq.) and A-11-2 were used instead of Compounds A-14-1 and A-14-2.
Compound A-15-3 (7.6 g, yield 58%, MS[M+H]+=952) was obtained in the same manner as in Synthesis Example 4 except that Compound A-15-2 (9.7 g, 1 eq.) was used instead of Compound A-2-3.
Compound A-15 (4.1 g, yield 71%, MS[M+H]+=1173) was obtained in the same manner as in Synthesis Example 3 except that Compounds A-15-3 (1 eq.) and S-26 (1.2 eq.) were used instead of Compounds A-2-1 and A-2-2.
After dissolving 1-bromo-3-chloro-5-tertbutylbenzene (121 mmol, 30 g) and 4-tertbutyl-N-(4-tertbutylphenyl)-2,6-dimethylaniline (121 mmol, 37.5 g) in toluene (0.2 M, 605 ml) in a 3-neck flask, sodium tertbutoxide (182 mmol, 17.5 g) and bis(tri-tertbutylphosphine)palladium(0) (1.2 mmol, 0.62 g) were introduced thereto, and the result was stirred for 4 hours under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then H2O was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound B-1-1 (51.2 g, yield 89%, MS[M+H]+=476).
After dissolving Compound S-27 (97.6 mmol, 30 g) and 4-tertbutylaniline (97.6 mmol, 14.6 g) in toluene (0.2 M, 488 ml) in a 3-neck flask, sodium tert-butoxide (146.5 mmol, 14.1 g) and bis(tri-tertbutylphosphine)palladium(0) (0.98 mmol, 0.5 g) were introduced thereto, and the result was stirred for 6 hours under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then H2O was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound B-1-2 (35.4 g, yield 97%, MS[M+H]+=376).
After dissolving Compound B-1-1 (44.1 mmol, 21 g) and Compound B-1-2 (44.1 mmol, 16.6 g) in toluene (0.2 M, 220 ml) in a 3-neck flask, sodium tert-butoxide (66.2 mmol, 6.4 g) and bis(tri-tertbutylphosphine)palladium(0) (0.44 mmol, 0.23 g) were introduced thereto, and the result was stirred for 6 hours under reflux under the argon atmosphere. When the reaction was finished, the result was cooled to room temperature, then H2O was introduced thereto, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried with MgSO4 and concentrated, and the sample was purified using silica gel column chromatography to obtain Compound B-1-3 (21.8 g, yield 61%, MS[M+H]+=815).
Compound B-1 (5.3 g, yield 21%, MS[M+H]+=957) was obtained in the same manner as in Synthesis Example 4 except that Compound B-1-3 (21.8 g, 1 eq.) was used instead of Compound A-2-3, and the stirring was conducted at 140° C.
Compound B-2-1 (15.2 g, yield 88%, MS[M+H]+=482) was obtained in the same manner as in Synthesis Example 1 except that Compound S-28 was used instead of Compound S-2.
Compound B-2-2 (12.6 g, yield 47%, MS[M+H]+=819) was obtained in the same manner as in Synthesis Example 6 except that Compounds B-2-1 (15 g, 1 eq.) and S-29 were used instead of Compounds A-1-1 and S-10.
Compound B-2 (3.5 g, yield 38%, MS[M+H]+=827) was obtained in the same manner as in Synthesis Example 51 except that Compound B-2-2 (9 g, 1 eq.) was used instead of Compound B-1-3.
Compound B-3-1 (11.1 g, yield 78%, MS[M+H]+=520) was obtained in the same manner as in Synthesis Example 1 except that Compound S-30 was used instead of Compound S-2.
Compound B-3-2 (8.7 g, yield 56%, MS[M+H]+=806) was obtained in the same manner as in Synthesis Example 6 except that Compounds B-3-1 (10 g, 1 eq.), S-31 and S-32 were used instead of Compounds A-1-1, S-9 and 5-10.
Compound B-3 (2.3 g, yield 26%, MS[M+H]+=813) was obtained in the same manner as in Synthesis Example 51 except that Compound B-3-2 (8.7 g, 1 eq.) was used instead of Compound B-1-3.
Compound B-4-1 (16.3 g, yield 73%, MS[M+H]+=524) was obtained in the same manner as in Synthesis Example 1 except that Compound S-33 was used instead of Compound S-2.
Compound B-4-2 (12.8 g, yield 52%, MS[M+H]+=918) was obtained in the same manner as in Synthesis Example 6 except that Compounds B-4-1 (14 g, 1 eq.), S-17 and S-27 were used instead of Compounds A-1-1, S-9 and 5-10.
Compound B-4 (2.8 g, yield 25%, MS[M+H]+=926) was obtained in the same manner as in Synthesis Example 51 except that Compound B-4-2 (11 g, 1 eq.) was used instead of Compound B-1-3.
Compound B-5-1 (19.1 g, yield 79%) was obtained in the same manner as in Synthesis Example 40 except that Compound S-34 was used instead of Compound S-2.
Compound B-5-2 (10.7 g, yield 72%, MS[M+H]+=609) was obtained in the same manner as in Synthesis Example 41 except that Compound B-5-1 (18 g, 1 eq.) and diphenylamine were used instead of Compounds A-14-1 and A-4-2.
Compound B-5-3 (7.8 g, yield 47%, MS[M+H]+=949) was obtained in the same manner as in Synthesis Example 6 except that Compounds B-5-2 (10.7 g, 1 eq.) and S-27 were used instead of Compounds A-1-1 and 5-10.
Compound B-5 (1.7 g, yield 21%, MS[M+H]+=957) was obtained in the same manner as in Synthesis Example 51 except that Compound B-5-3 (7.8 g, 1 eq.) was used instead of Compound B-1-3.
Compound B-6-1 (20.1 g, yield 80%, MS[M+H]+=493) was obtained in the same manner as in Synthesis Example 1 except that Compound S-34 was used instead of Compound S-1.
Compound B-6-2 (20.6 g, yield 70%, MS[M+H]+=376) was obtained in the same manner as in Synthesis Example 49 except that Compound S-35 was used instead of Compound S-27.
Compound B-6-3 (21.2 g, yield 69%, MS[M+H]+=833) was obtained in the same manner as in Synthesis Example 3 except that Compounds B-6-1 (19.4 g, 1 eq.) and B-6-2 were used instead of Compounds A-2-1 and A-2-2.
Compound B-6 (1.3 g, yield 12%, MS[M+H]+=841) was obtained in the same manner as in Synthesis Example 51 except that Compound B-6-3 (11 g, 1 eq.) was used instead of Compound B-1-3.
Compound S-36 (30 g, 93.10 mmol) and Compound S-37 (15.28 g, 97.76 mmol) were completely dissolved in tetrahydrofuran (THF) (300 mL) in a 500 mL round bottom flask under the nitrogen atmosphere. K2CO3 (38.6 g, 279.32 mmol) dissolved in distilled water (100 ml) was added to the tetrahydrofuran (THF) solution, and after introducing [1,1′-bis(diphenylphosphino) ferrocene]palladium(II) dichloride (0.34 g, 0.46 mmol) thereto, the result was stirred for 5 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the tetrahydrofuran (THF), recrystallized with ethyl acetate (EA) (240 mL) to prepare C-1-1 (27.67 g, yield: 84%).
MS [M+H]+=354
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-38 (9.26 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-1 (16.06 g, yield: 89%).
MS[M+H]+=639
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-39 (10.42 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-2 (15.73 g, yield: 82%).
MS[M+H]+=679
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-40 (12.15 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-3 (18.37 g, yield: 85%).
MS[M+H]+=739
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-41 (12.15 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-4 (16.70 g, yield: 80%).
MS[M+H]+=739
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-42 (11.80 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-5 (18.08 g, yield: 88%).
MS[M+H]+=727
After completely dissolving Compound C-1-1 (10 g, 28.26 mmol) and Compound S-43 (10.19 g, 28.82 mmol) in toluene (100 mL) in a 500 mL round bottom flask under the nitrogen atmosphere, NaOtBu (3.80 g, 39.56 mmol) was added thereto, and after introducing bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) thereto, the result was stirred for 3 hours while heating. The result was cooled to room temperature, filtered to remove the base, and, after vacuum concentrating the toluene, recrystallized with ethyl acetate (200 mL) to prepare C-6 (14.02 g, yield: 76%).
MS[M+H]+=653
A glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 Å was placed in detergent-dissolved distilled water and ultrasonic cleaned. Herein, a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After the cleaning with distilled water was finished, the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition apparatus.
On the transparent ITO electrode prepared as above, compounds of the following Compound HT1 and the following Compound HI were thermal vacuum deposited in a ratio of 97:3 (molar ratio) to a thickness of 100 Å to form a hole injection layer. A hole transfer layer was formed on the hole injection layer by vacuum depositing a compound represented by the following Chemical Formula HT1 (1100 Å). Then, an electron blocking layer was formed on the hole transfer layer by vacuum depositing Compound C-1 to a film thickness of 50 Å.
Subsequently, a light emitting layer was formed on the electron blocking layer by vacuum depositing a compound represented by the following Chemical Formula BH and Compound A-1 in a weight ratio of 25:1 to a film thickness of 200 Å.
On the light emitting layer, an electron transfer layer was formed by vacuum depositing a compound represented by the following Chemical Formula ET1 to a film thickness of 50 Å. Then, an electron injection layer was formed on the electron transfer layer to a thickness of 310 Å by vacuum depositing a compound represented by the following Chemical Formula ET2 and a compound represented by the following Chemical Formula LiQ in a weight ratio of 1:1. On the electron injection layer, a cathode was formed by consecutively depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å.
In the above-described process, the deposition rates of the organic materials were maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rates of the lithium fluoride and the aluminum of the cathode were maintained at 0.3 Å/sec and 2 Å/sec, respectively, and the degree of vacuum during the deposition was maintained at 2×10−7 torr to 5×10−6 torr, and as a result, an organic light emitting device was manufactured.
Organic light emitting devices were manufactured in the same manner as in Example 1 except that the electron blocking layer and the dopant of the light emitting layer were changed as in the following Table 1.
Organic light emitting devices were manufactured in the same manner as in Example 1 except that the electron blocking layer and the dopant of the light emitting layer were changed as in the following Table 1.
For each of the organic light emitting devices manufactured in the examples and the comparative examples, voltage, efficiency, color coordinate and lifetime were measured when applying a current of 10 mA/cm2, and the results are shown in the following Table 1. T95 means time taken for luminance to decrease to 95% from initial luminance (1600 nit).
From Table 1, it was seen that the device including the light emitting layer including Chemical Formula 1 and the first organic material layer including Chemical Formula 2 of the present disclosure had properties of high efficiency, low voltage and long lifetime.
Specifically, compared to Comparative Examples 1, 2 and 7 including BD1 and BD2 in which benzene is fused to the core unlike Chemical Formula 1 of the present disclosure, the devices of Examples 1 to 69 of the present disclosure had high efficiency and lifetime, and low voltage. In addition, compared to Comparative Examples 3 to 7 including HT1 to HT4 with different biphenylene orientation or different linking position of carbazole unlike Chemical Formula 2 of the present disclosure, the devices of Examples 1 to 69 of the present disclosure had high efficiency and lifetime, and low voltage.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2019-0156840 | Nov 2019 | KR | national |
This application is a National Stage Application of International Application No. PCT/KR2020/017106, filed on Nov. 27, 2020, which claims priority to Korean Patent Application No. 10-2019-0156840, filed on Nov. 29, 2019, the disclosures of which are incorporated herein by reference in their entirety.
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/KR2020/017106 | 11/27/2020 | WO |
