KR20180015794A - Aromatic compound and organic electroluminescence device including the same - Google Patents

Abstract

The present invention relates to an aromatic compound and an organic electroluminescence device comprising the same. According to one example of the present invention, the aromatic compound is represented by chemical formula 1. In the chemical formula 1: at least two of R_1 to R_4 are each independently a substituted or unsubstituted alkyl group having 1-30 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6-30 carbon atoms, or a substituted or unsubstituted ring-forming hetero aryl group having 2-30 carbon atoms; A is an electron-accepting substituent; and D is an electron-donating substituent.

Description

TECHNICAL FIELD [0001] The present invention relates to an aromatic compound and an organic electroluminescent device including the same. BACKGROUND ART [0002] AROMATIC COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE INCLUDING THE SAME [0003]

The present invention relates to an aromatic compound and an organic electroluminescent device including the aromatic compound.

As an image display apparatus, an organic electroluminescence display has been actively developed. The organic electroluminescence display device differs from a liquid crystal display device and the like and includes a so-called organic electroluminescence display device which recombines holes and electrons injected from a first electrode and a second electrode in a light emitting layer to realize a display by realizing a light emitting material, Emitting display device.

Examples of the organic electroluminescent device include a first electrode, a hole transporting layer disposed on the first electrode, a light emitting layer disposed on the hole transporting layer, an electron transporting layer disposed on the light emitting layer, and a second electrode disposed on the electron transporting layer Organic devices constructed are known. Holes are injected from the first electrode, and the injected holes move into the hole transport layer and are injected into the light emitting layer. On the other hand, electrons are injected from the second electrode, and the injected electrons move into the electron transport layer and are injected into the light emitting layer. Electrons injected into the light emitting layer are recombined with each other to form excitons in the light emitting layer. The organic electroluminescent device emits light by using light generated when the excitons fall back to the ground state. Further, the organic electroluminescent device is not limited to the above-described configuration, and various modifications are possible.

An object of the present invention is to provide an aromatic compound and an organic electroluminescent device including the aromatic compound. More specifically, it is an object of the present invention to provide an aromatic compound for thermal activation retardation fluorescent material and an organic electroluminescent device including the same.

One embodiment of the present invention provides an aromatic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula (1), R ₁ to R ₄ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in the ring or a substituted or unsubstituted At least two of R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 or more carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, A is represented by any one of the following formulas (2-1) to (2-11)

[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Chemical Formula 2-4] [Chemical Formula 2-5]

[Chemical Formula 2-6] [Chemical Formula 2-7]

[Chemical Formula 2-8] [Chemical Formula 2-9]

[Chemical Formula 2-10] [Chemical Formula 2-11]

In formulas (2-1) to (2-11), Q ₁ to Q ₁₅ each independently represent a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring- An unsubstituted heteroaryl group having from 2 to 30 carbon atoms in the ring-

a, d, e, f, g, m, n and o are each independently an integer of 0 to 4,

b, c, h, i, j, k and l are each independently an integer of 0 to 3,

In Formula 1,

D is represented by the following formula (3-1) or (3-2).

[Formula 3-1] [Formula 3-2]

In Formulas (3-1) and (3-2), L ₁ and L ₂ are each independently a direct linkage or a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms and R ₅ to R ₂₂ are A halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, Or a heteroaryl group having an unsubstituted ring-forming carbon number of 2 or more and 30 or less, X is CRaRb, SiRcRd, GeReRf, NRg, O or S, Ra to Rg each independently represent a substituted or unsubstituted ring- Or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, Ra and Rb, Rc and Rd, and Re and Rf may combine with each other to form a ring.

The formula (1) may be represented by any one of the following formulas (1-1) to (1-4).

[Formula 1-1] [Formula 1-2]

[Chemical Formula 1-3] [Chemical Formula 1-4]

In formulas 1-1 to 1-4, R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, And a heteroaryl group having an unsubstituted ring-forming carbon number of 2 or more and 30 or less, and A and D are the same as described above.

At least two of R ₁ to R ₄ each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

At least two of R ₁ to R ₄ may be independently a methyl group or a phenyl group.

D is represented by the above formula (3-2), X is CRaRb, and Ra and Rb may be the same as described above.

D may be represented by any one of the following formulas (3-2-1) to (3-2-5).

[Formula 3-2-1] [Formula 3-2-2]

[Formula 3-2-3] [Formula 3-2-4]

[Chemical Formula 3-2-5]

In Formulas (3-2-1) to (3-2-5), L ₂ , R ₁₅ to R ₁₇ and R ₂₀ to R ₂₂ are the same as described above.

L ₁ and L ₂ each independently may be a direct bond.

An embodiment of the present invention includes a first electrode, a hole transporting region provided on the first electrode, a light emitting layer provided on the hole transporting region, an electron transporting region provided on the light emitting layer, and a second electrode provided on the electron transporting region, At least one of the hole transporting region, the light emitting layer, and the electron transporting region includes the aromatic compound according to one embodiment of the present invention.

The aromatic compound represented by the general formula (1) may be contained in the light emitting layer.

The aromatic compound represented by formula (1) may have an absolute value of singlet energy level and triplet energy level difference of 0.2 eV or less.

The aromatic compound represented by the formula (1) may be a material for thermal activation delayed fluorescent light emission.

The compound according to an embodiment of the present invention can be used as a material for an organic electroluminescence device.

The compound according to one embodiment of the present invention can be used as a material for retarded fluorescent light emission.

The organic electroluminescent device according to an embodiment of the present invention including the compound according to one embodiment of the present invention can realize blue light emission at the same time as improving efficiency and reducing roll-off.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.

The above objects, other objects, features and advantages of the present invention will be more readily understood from the accompanying drawings and the following preferred embodiments. However, the present invention is not limited to the embodiments described herein but may be embodied in other forms. Rather, the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art.

Like reference numerals are used for like elements in describing each drawing. In the accompanying drawings, the dimensions of the structures are shown enlarged from the actual for the sake of clarity of the present invention. The terms first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component. The singular expressions include plural expressions unless the context clearly dictates otherwise.

In this specification, the terms "comprises" or "having" and the like refer to the presence of stated features, integers, steps, operations, elements, components, or combinations thereof, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof. Also, where a portion such as a layer, film, region, plate, or the like is referred to as being "on" another portion, this includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. On the contrary, when a part such as a layer, film, region, plate or the like is referred to as being "under" another part, it includes not only the case where it is "directly underneath" another part but also another part in the middle.

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

As used herein, the term "substituted or unsubstituted" means a group selected from the group consisting of a deuterium atom, a halogen group, a cyano group, a nitro group, an amino group, a silyl group, a boron group, an arylamine group, a phosphine oxide group, a phosphine sulfide group, , An aryl group, and a heterocyclic group, which may be substituted or unsubstituted. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, the biphenyl group may be interpreted as an aryl group and may be interpreted as a phenyl group substituted with a phenyl group.

In the present specification, the terms "combined with each other to form a ring" may mean to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. The hydrocarbon ring and the heterocycle may be monocyclic or polycyclic. Further, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.

In the present specification, examples of the halogen group include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

In the present specification, the alkyl group may be linear, branched or cyclic. The number of carbon atoms of the alkyl group is 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 15 or less, 1 or more or 10 or less or 1 or more and 6 or less. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, butylhexyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-t-butylcyclohexyl group, an n-heptyl group, a 1-methylhexyl group, a 1-methylhexyl group, Methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, N-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-hexyldecyl group, N-heptyldodecyl group, n-tridecyl group, n-tetradecyl group, n-tetradecyl group, n-pentadecyl group, - PENTADE N-hexadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, An n-hexyl eicosyl group, an n-hexyl group, an n-docosyl group, an n-tricosyl group, an n-tricyclohexyl group, -Tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group and n-triacontyl group. It does not.

As used herein, an aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The ring-forming carbon number of the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quinphenyl group, a sexphenyl group, a triphenylene group, a pyrenyl group, a benzofluoranthenyl group, And the like, but are not limited thereto.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

In the present specification, the heteroaryl group may be a heteroaryl group containing at least one of O, N, P, Si, Ge and S as a hetero atom. The ring-forming carbon number of the heteroaryl group is 2 or more and 30 or less or 2 or more and 20 or less. Examples of the heteroaryl group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, An isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, A benzothiazolyl group, a phenothiazyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, Dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the description of the aryl group described above can be applied except that the arylene group is a divalent group.

In the present specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. It is not limited.

In the present specification, the boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a diphenylboron group, and a phenylboron group.

In the present specification, the alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is 2 or more and 30 or less, 2 or more and 30 or less or 2 or more and 10 or less. Examples of the alkenyl group include, but are not limited to, a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1,3-butadienylaryl group, a styryl group and a styryl vinyl group.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include an alkylamine group and an arylamine group. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group and a triphenylamine group.

Hereinafter, an aromatic compound according to an embodiment of the present invention will be described.

An aromatic compound according to an embodiment of the present invention is represented by the following formula (1).

[Chemical Formula 1]

In Formula (1), R ₁ to R ₄ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in the ring or a substituted or unsubstituted And a heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms.

In formula (1), at least two of R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, And a heteroaryl group having 2 or more and 30 or less carbon atoms in the ring. That is, in the formula (1), at least two of R ₁ to R ₄ are substituted with a substituent which is not a hydrogen atom.

In formula (1), A is represented by any one of the following formulas (2-1) to (2-11).

[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Chemical Formula 2-4] [Chemical Formula 2-5]

[Chemical Formula 2-6] [Chemical Formula 2-7]

[Chemical Formula 2-8] [Chemical Formula 2-9]

[Chemical Formula 2-10] [Chemical Formula 2-11]

In formulas (2-1) to (2-11), Q ₁ to Q ₁₅ each independently represent a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring- A, d, e, f, g, m, n and o are each independently an integer of 0 to 4, and b, c, h, i, j, k and l are each independently an integer of 0 to 3;

In the formula (2-1), when a is 2 or more, plural Q1 are the same or different from each other.

In formula (2-2), when b is 2 or more, plural Q2 are the same or different from each other.

In formula (2-3), when c is 2 or more, plural Q3 are the same or different from each other.

In formula (2-4), when d is 2 or more, plural Q4 are the same or different, and when e is 2 or more, plural Q5 are the same or different from each other.

In the formula (2-5), when f is 2 or more, a plurality of Q 6 are the same or different from each other, and when g is 2 or more, the plurality of Q 7 are the same or different from each other.

In the formulas 2-6, when h is 2 or more, plural Q8 are the same or different from each other.

In formula (2-7), when i is 2 or more, plural Q9 are the same or different from each other.

In formula (2-8), when j is 2 or more, a plurality of Q10 are the same or different from each other.

In the formula (2-9), when k is 2 or more, a plurality of Q11 are the same or different from each other.

In formula (2-10), when l is 2 or more, plural Q12 are the same or different, and when m is 2 or more, plural Q13 are the same or different from each other.

In the general formula (2-11), when n is 2 or more, a plurality of Q14s are the same as or different from each other, and when o is 2 or more, the plurality of Q15s are the same or different from each other.

In formula (2-1), a may be 0.

In formula (2-1), a is an integer of 1 or more and 4 or less, and each of Q1 may independently be a substituted or unsubstituted heteroaryl group having 2 or more ring-forming carbon atoms.

In formula (2-2), b may be 0. However, it is not limited thereto, and in Formula 2-2, b may be an integer of 1 or more and 3 or less.

In formula (2-3), c may be 0.

In formula (2-3), c is an integer of 1 or more and 3 or less, and each of Q3 independently represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 or more ring- have.

In formula 2-4, d + e = 0.

In Formula 2-4, at least one of d and e is an integer of 1 to 4, and at least one of Q4 and Q5 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

In Formula 2-5, f + g = 0.

In Formula 2-5, at least one of f and g is an integer of 1 to 4, and at least one of Q6 and Q7 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

In Formula 2-6, h may be 0.

In formula (2-6), h is an integer of 1 or more and 3 or less, and each Q8 independently represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring- .

In Formula 2-7, i may be 0. However, it is not limited thereto, and in Formula 2-7, i may be an integer of 1 or more and 3 or less.

In Formulas 2-8, j may be 0.

In Chemical Formula 2-8, j is an integer of 1 or more and 3 or less, and each of Q10 is independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms .

In Formulas 2-9, k may be 0.

In Chemical Formula (2-9), k is an integer of 1 or more and 3 or less, and each Q11 independently represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring- .

In formula 2-10, l + m = 0.

At least one of Q12 and Q13 is independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic carbon number 6 Or more and 30 or less.

In formula (2-11), n + o = 0.

In formula (2-11), at least one of n and o is an integer of 1 to 4, and at least one of Q14 and Q15 is independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted ring Or an aryl group having 6 or more and 30 or less carbon atoms.

In formula (1), D is represented by the following formula (3-1) or (3-2).

[Formula 3-1] [Formula 3-2]

In Formulas (3-1) and (3-2), L ₁ and L ₂ each independently represent a direct linkage or a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms.

In this specification, "direct linkage" may include a single bond.

In formulas (3-1) and (3-2), R ₅ to R ₂₂ each independently represent a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, Or an unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In the formula (3-2), X is CRaRb, SiRcRd, GeReRf, NRg, O or S, and Ra to Rg each independently represent a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted ring And a heteroaryl group having from 2 to 30 carbon atoms.

In Formula (3-2), when X is CRaRb, Ra and Rb may be bonded to each other to form a ring.

In Formula (3-2), when X is SiRcRd, Rc and Rd may be bonded to each other to form a ring.

In the formula (3-2), when X is GeReRf, Re and Rf may be bonded to each other to form a ring.

An aromatic compound according to an embodiment of the present invention includes an electron acceptor, an electron donor, and a linker. Specifically, the substituted phenylene group represented by the general formula (1) is a linker, A in the general formula (1) is an electron acceptor, and D is an electron donor.

An aromatic compound according to one embodiment of the present invention comprises at least a disubstituted bulky linker. "At least disubstituted" means that the phenylene group is substituted by two or more, in addition to the electron acceptor represented by A and the electron donor represented by D.

For example, the formula (1) may be represented by any one of the following formulas (1-1) to (1-4).

[Formula 1-1] [Formula 1-2]

[Chemical Formula 1-3] [Chemical Formula 1-4]

In formulas 1-1 to 1-4, R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, And a heteroaryl group having 2 or more and 30 or less unsubstituted ring-forming carbon atoms, and A and D are the same as described above. That is, in formulas 1-1 to 1-4, R ₁ to R ₄ are each independently substituted with a substituent other than a hydrogen atom.

The aromatic compounds represented by formulas (1-1), (1-2), and (1-3) are connected through an electron acceptor represented by A and a linker in which an electron donor represented by D is a phenylene group that is disubstituted.

The aromatic compound represented by the general formula (1-4) is connected through an electron acceptor represented by A and a linker in which an electron donor represented by D is a tetra-substituted phenylene group. The aromatic compound represented by the general formula (1-4) includes a linker having a large steric effect as compared with the aromatic compound represented by the general formula (1-1), (1-2) or (1-3).

However, the present invention is not limited thereto, and the aromatic compound represented by the general formula (1) may be connected to the electron acceptor represented by A and the electron donor represented by D via a linker which is a tri-substituted phenylene group.

In formula (1), at least two of R ₁ to R ₄ may each independently be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

In Formula (1), at least two of R ₁ to R ₄ may be independently a methyl group or a phenyl group.

The formula (1) may be represented by any one of the following formulas.

Ph in the structural formulas means a phenyl group.

In formula (1), D may be represented by formula (3-2), and X in formula (3-2) may be CRaRb. The definitions of Ra and Rb are the same as described above.

In formula (1), D may be represented by the following formula (3-2-1).

[Formula 3-2-1]

For example, in Formula 1, D may be represented by any one of the following Formulas 3-2-2 to 3-2-5.

[Formula 3-2-2] [Formula 3-2-3]

[Formula 3-2-4] [Formula 3-2-5]

In formulas (3-2-1) to (3-2-5), L ₂ , R ₁₅ to R ₁₇ and R ₂₀ to R ₂₂ are the same as defined in claim 1.

In formula (3-2-1), L ₂ is a direct bond, and R ₁₅ to R ₁₇ and R ₂₀ to R ₂₂ are hydrogen atoms. In the formula (3-2-1), L ₂ is a direct bond, R ₁₇ and R ₂₀ are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms and R ₁₅ , R ₁₆ , R ₂₁ and R ₂₂ are hydrogen atoms Lt; / RTI > In formula (3-2-1), L ₂ is a direct bond, R ₁₇ and R ₂₀ are methyl groups, and R ₁₅ , R ₁₆ , R ₂₁ and R ₂₂ are hydrogen atoms.

In Formulas (3-2-2) to (3-2-5), L ₂ is a direct bond, and R ₁₅ to R ₁₇ and R ₂₀ to R ₂₂ are hydrogen atoms. Formula in 3-2-2 to 3-2-5, L ₂ is a direct bond, R ₁₇ and R ₂₀ is an alkyl group of 1 to carbon atoms, substituted or unsubstituted _{30, R 15, R 16,} R 21 , and And R < ₂₂ > may be a hydrogen atom. In formulas (3-2-2) to (3-2-5), L ₂ is a direct bond, R ₁₇ and R ₂₀ are methyl groups, and R ₁₅ , R ₁₆ , R ₂₁ and R ₂₂ are hydrogen atoms.

In Formulas (3-1) and (3-2), L ₁ and L ₂ each independently may be a direct bond or a phenylene group.

In formulas (3-1) and (3-2), L ₁ and L ₂ each independently may be a direct bond.

The aromatic compound represented by the general formula (1) may be at least one selected from the compounds represented by the following general formula (1). Ph in the following compounds means a phenyl group.

[Compound group 1]

.

.

The aromatic compound according to one embodiment of the present invention can be used as a thermally active retarding fluorescent material. The aromatic compound according to an embodiment of the present invention may emit blue light through thermal activation delay fluorescence. The aromatic compound according to one embodiment of the present invention can realize blue light emission with high efficiency.

The aromatic compound according to an embodiment of the present invention may introduce rollers having a large steric hindrance (bulky) to achieve a roll-off reduction effect by only the dye-sensitized photocatalyst.

Hereinafter, an organic electroluminescent device according to an embodiment of the present invention will be described. Hereinafter, the difference from the aromatic compound according to one embodiment of the present invention described above will be described in detail, and the unexplained portion will depend on the aromatic compound according to one embodiment of the present invention described above.

An organic electroluminescent device according to an embodiment of the present invention includes an aromatic compound according to an embodiment of the present invention.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.

1 and 2, an organic electroluminescent device 10 according to an embodiment of the present invention includes a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, And a second electrode EL2.

The first electrode EL1 has conductivity. The first electrode EL1 may be a pixel electrode or an anode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is formed of a transparent metal oxide such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO tin zinc oxide) and the like. The first electrode EL1 may be formed of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Or a transparent conductive film formed of a reflective film or a semi-transmissive film formed of the above material and indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide Lt; / RTI >

The hole transporting region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, and an electron blocking layer. The thickness of the hole transporting region (HTR) may be, for example, about 200 Å to about 3000 Å.

The hole transporting region (HTR) may have a single layer of a single material, a single layer of a plurality of different materials, or a multi-layer structure having a plurality of layers of a plurality of different materials.

For example, the hole transporting region (HTR) may have a single layer structure of a hole injection layer (HIL) or a hole transporting layer (HTL), or may have a single layer structure of a hole injecting material and a hole transporting material. The hole transporting region HTR may have a structure of a single layer made of a plurality of different materials or may have a hole injection layer (HIL) / hole transporting layer (HTL), a hole injection layer (HIL) / hole transport layer (HTL) / hole buffer layer, hole injection layer (HIL) / hole buffer layer, hole transport layer (HTL) / hole buffer layer or hole injection layer (HIL) / hole transport layer Structure, but is not limited thereto.

The hole transporting region HTR can be formed by a variety of methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett, inkjet printing, laser printing, and laser induced thermal imaging .

The hole injection layer (HIL) may include, for example, a phthalocyanine compound such as copper phthalocyanine; (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine, m- , 4 "-tris (3-methylphenylphenylamino) triphenylamine), TDATA (4,4'4" -Tris (N, N-diphenylamino) triphenylamine) (2-naphthyl) -N-phenylamino} -triphenylamine, PEDOT / PSS, poly (4-styrenesulfonate), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA / Camphor sulfonicacid), PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate), NPB (Naphthylen-1-yl) -N, N'- (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis (pentafluorophenyl) borate], HAT-CN (dipyrazino [2,3-f: 2 ', 3'-h] quinoxaline-2,3 , 6,7,10,11-hexacarbonitrile), and the like.

The hole transporting layer (HTL) may be formed by, for example, a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine-based derivative, TPD (N, N'- Triphenylamine derivatives such as N'-diphenyl- [1,1-biphenyl] -4,4'-diamine and TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine) , N'-di (naphthalene-1-yl) -N, N'-diphenyl-benzidine), TAPC (4,4'-Cyclohexylidene bis [N, , 4'-Bis [N, N '- (3-tolyl) amino] -3,3'-dimethylbiphenyl).

The thickness of the hole transporting region (HTR) may be from about 100 A to about 10,000 A, e.g., from about 100 A to about 1000 A. When the hole transporting region HTR includes both the hole injecting layer HIL and the hole transporting layer HTL, the thickness of the hole injecting layer HIL is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, The thickness of the hole transporting layer (HTL) may be about 30 Å to about 1000 Å. When the thickness of the hole transporting region (HTR), the hole injecting layer (HIL), and the hole transporting layer (HTL) satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantial increase in drive voltage.

In addition to the above-mentioned materials, the hole transporting region (HTR) may further include a charge generating material for improving conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transporting region (HTR). The charge generating material may be, for example, a p-dopant. The p-dopant may be, but is not limited to, one of quinone derivatives, metal oxides, and cyano group-containing compounds. For example, non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,4,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide But the present invention is not limited thereto.

As described above, the hole transporting region HTR may further include at least one of a hole blocking layer and an electron blocking layer in addition to the hole injecting layer (HIL) and the hole transporting layer (HTL). The hole buffer layer can increase the light emission efficiency by compensating the resonance distance according to the wavelength of light emitted from the light emitting layer (EML). As the material contained in the hole buffer layer, a material that can be included in the hole transport region (HTR) may be used. The electron blocking layer is a layer that prevents the injection of electrons from the electron transporting region (ETR) to the hole transporting region (HTR).

The light emitting layer (EML) is provided on the hole transporting region (HTR). The thickness of the light emitting layer (EML) may be, for example, about 100 Å to about 1000 Å. The light emitting layer (EML) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layered structure having a plurality of layers made of a plurality of different materials.

The aromatic compound according to one embodiment of the present invention is included in at least one of a hole transporting region (HTR), a light emitting layer (EML), and an electron transporting region (ETR).

Hereinafter, the aromatic compound according to one embodiment of the present invention is included in the light emitting layer (EML). However, the present invention is not limited thereto, and the aromatic compound according to an embodiment of the present invention may be included in at least one layer of one or more organic layers provided between the first electrode EL1 and the second electrode EL2. For example, an aromatic compound according to an embodiment of the present invention may be included in a hole transporting region (HTR). For example, the aromatic compound according to one embodiment of the present invention may be contained in a hole transporting layer (HTL).

The light emitting layer (EML) may include an aromatic compound according to an embodiment of the present invention. Specifically, the light-emitting layer (EML) may include a halogen-containing compound represented by the following general formula (1).

[Chemical Formula 1]

The detailed description of R ₁ to R ₄ , A and D will be omitted.

The light emitting layer (EML) may contain one or more aromatic compounds represented by the general formula (1). The light-emitting layer (EML) may further comprise a known material other than the aromatic compound represented by the general formula (1). For example, spiro-DPVBi, spiro-6P, 2,2 ', 7,7'-tetrakis (biphenyl-4-yl) -9,9'-spirobifluorene ), A fluorescent material including any one selected from the group consisting of distyryl-benzene (DSB), distyryl-arylene (DSA), polyfluorene (PFO), and poly (p-phenylene vinylene) However, the present invention is not limited thereto.

The aromatic compound according to an embodiment of the present invention may be included in the light emitting layer (EML) to emit retarded fluorescent light. The aromatic compound represented by the formula (1) may be a material for retarding fluorescence. The aromatic compound represented by formula (1) may be a material for thermal activation retardation fluorescence (TADF).

The aromatic compound according to an embodiment of the present invention may be a thermal activation retardation fluorescent material for emitting blue light. The aromatic compound according to an embodiment of the present invention may emit blue light having a wavelength range of less than about 470 nm and emit blue light having a wavelength range of about 440 nm to about 470 nm or about 450 nm to about 470 nm .

An aromatic compound according to an embodiment of the present invention may have an absolute value of a singlet energy level and a triplet energy level difference of 0.2 eV or less. It is possible to efficiently emit thermally-activated delayed fluorescence by controlling the sagittal-triplet energy gap to be small.

The light emitting layer (EML) may further include a host. For example, Alq ₃ (tris (8-hydroxyquinolino) aluminum), CBP (4,4'-bis (N-carbazolyl) -1,1'-biphenyl) , PVK (n-vinylcabazole), ADN (naphthalene-2-yl) anthracene, TCTA (4,4 ', 4 "-tris (carbazol- TPBi (1,3,5-tris (N-phenylbenzimidazole-2-yl) benzene), TBADN (3-tert-butyl-9,10-di (naphth- (2-Methyl-9,10-bis (naphthalen-2-yl) anthracene), DPEPO ( bis [2 - (diphenylphosphino) phenyl] ether oxide ), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis (triphenylsilyl) benzene), DPSiO 3 (Hexaphenylcyclotrisiloxane), DPSiO 4 (Octaphenylcyclotetra siloxane), PPF (2,8-Bis ( diphenylphosphoryl) dibenzofuran) and the like can be used.

The light emitting layer (EML) may have a thickness of, for example, about 100 A to about 1000 A.

An electron transporting region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include, but is not limited to, at least one of an electron blocking layer, an electron transport layer (ETL), and an electron injection layer (EIL).

The electron transport region (ETR) may have a single layer of a single material, a single layer of a plurality of different materials, or a multi-layer structure having a plurality of layers of a plurality of different materials.

For example, the electron transport region (ETR) may have a single layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or may have a single layer structure of an electron injecting material and an electron transporting material. In addition, the electron transport region (ETR) may have a structure of a single layer made of a plurality of different materials, an electron transport layer (ETL) / electron injection layer (EIL) sequentially stacked from the first electrode (AN) Layer / electron transport layer (ETL) / electron injection layer (EIL) structure. The thickness of the electron transporting region (ETR) may be, for example, from about 1000 A to about 1500 A thick.

The electron transport region (ETR) can be formed by a variety of methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett, inkjet printing, laser printing, and laser induced thermal imaging .

If the electron transport region (ETR) is an electron transport layer (ETL), an electron transport region (ETR) is _{Alq 3 (Tris (8-hydroxyquinolinato} ) aluminum), 1,3,5-tri [(3-pyridyl) - 3-yl] benzene, 2,4,6-tris (3 '- (pyridin-3-yl) biphenyl-3-yl) -1,3,5-triazine, 2- (4- (N-phenylbenzoimidazolyl -1-ylphenyl) -9,10-dinaphthylthracene, TPBi (1,3,5-Tri (1-phenyl-1H-benzo [d] imidazol- , 7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3- (4-Biphenylyl) -4-phenyl- , 4-triazole), NTAZ (4- (Naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazole), tBu- 4-tert-butylphenyl) -1,3,4- oxadiazole), BAlq (Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum), Bebq 2 but are not limited to, berylliumbis (benzoquinolin-10-olate), ADN (9,10-di (naphthalene-2-yl) anthracene) From about 100 A to about 10000 A, e.g., from about 1000 A to about 1500 A. When the thickness of the electron transporting layer (ETL) satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantial increase in driving voltage.

The electron transport region (ETR) The electron injection layer when comprise (EIL), an electron transport region (ETR) is a lanthanide metal such as LiF, LiQ (Lithium quinolate), Li 2 O, BaO, NaCl, CsF, Yb, Or metal halides such as RbCl and RbI, but the present invention is not limited thereto. The electron injection layer (EIL) may also be made of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Specifically, for example, the organometallic salt includes a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate or a metal stearate . The thickness of the electron injection layer (EIL) may be from about 1 A to about 100 A, from about 3 A to about 90 A. When the thickness of the electron injection layer (EIL) satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantial increase in driving voltage.

The electron transport region (ETR) may include a hole blocking layer, as mentioned above. The hole blocking layer may comprise, for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline) However, the present invention is not limited thereto.

And the second electrode EL2 is provided on the electron transporting region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO tin zinc oxide, and the like.

The second electrode EL2 may be formed of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Or a transparent conductive film formed of a reflective film or a semi-transmissive film formed of the above material and indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide Lt; / RTI >

Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

In the organic electroluminescent device 10, as a voltage is applied to the first electrode EL1 and the second electrode EL2, the holes injected from the first electrode EL1 pass through the hole transport region HTR And the electrons injected from the second electrode EL2 are transferred to the light emitting layer (EML) through the electron transporting region (ETR). The electrons and the holes are recombined in the light emitting layer (EML) to generate an exciton, and the excitons emit as they fall from the excited state to the ground state.

When the organic electroluminescent device 10 is of the top emission type, the first electrode EL1 may be a reflective electrode and the second electrode EL2 may be a transmissive electrode or a transflective electrode. When the organic electroluminescent device 10 is of the bottom emission type, the first electrode EL1 may be a transmissive electrode or a transflective electrode, and the second electrode EL2 may be a reflective electrode.

An organic electroluminescent device according to an embodiment of the present invention includes an aromatic compound represented by formula (1). The aromatic compound represented by the general formula (1) includes a bulky linker. The organic electroluminescent device according to one embodiment of the present invention has an effect of improving the efficiency and reducing the roll-off and simultaneously emitting blue light by including the compound in which the linker having a large stereoscopic effect is incorporated.

Hereinafter, the present invention will be described in more detail with reference to specific examples and comparative examples. The following examples are provided to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

(Synthesis Example)

The aromatic compound according to one embodiment of the present invention can be synthesized, for example, as follows. However, the method of synthesizing an aromatic compound according to an embodiment of the present invention is not limited thereto.

1. Synthesis of Compound 127

Compound 55, which is an aromatic compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

1.00 g of Compound A, 3.50 g of Compound B and 1.78 g of Pd (PPh ₃ ) ₄ 0.96 g K ₃ PO ₄ were added to a 100 mL three-necked flask under an atmosphere of argon (Ar), and the mixture was heated under reflux in 50 mL of toluene for 8 hours . After air cooling, water was added to separate the organic layer, and the solvent was distilled. The obtained crude product was purified by silica gel column chromatography (dichloromethane and hexane mixed solvent) and then recrystallized from a toluene / hexane mixed solvent to obtain 2.50 g of a white solid compound 69%).

The molecular weight of the compound measured by FAB-MS measurement was 870. From the above results, it was confirmed that the compound of white solid was Compound 127.

2. Synthesis of Compound 123

Argon (Ar) atmosphere, the compound A three-necked flask of 100mL 1.80g, Compound C 3.27g, by the addition of _{Pd (PPh 3) 4 1.74g K} 3 PO 4 3.20g, was refluxed for 6 hours heating in a toluene solvent in 50mL . After air cooling, water was added to separate the organic layer, and the solvent was distilled. The obtained crude product was purified by silica gel column chromatography (dichloromethane and hexane mixed solvent) and then recrystallized from a toluene / hexane mixed solvent to obtain 3.8 g of a white solid compound 85%).

The molecular weight of the compound measured by FAB-MS measurement was 593. From the above results, it was confirmed that the compound of the white solid was Compound 123.

3. Synthesis of Compound 124

Argon (Ar) atmosphere, was added 1.50g of the compound A, compound _{D 3.70g, Pd (PPh 3)} 4 1.45g K 3 PO 4 2.66g in 100mL three-necked flask, was heated at refluxing for 6 hours in toluene solvent in 80mL . After air cooling, water was added to separate the organic layer, and the solvent was distilled. The obtained crude product was purified by silica gel column chromatography (dichloromethane and hexane mixed solvent), and recrystallized from a toluene / hexane mixed solvent to obtain 3.2 g of a white solid compound (yield: 82%).

The molecular weight of the compound measured by FAB-MS measurement was 621. From the above results, it was confirmed that the compound of white solid was Compound 124.

 (Device fabrication)

The organic electroluminescent devices of Examples 1 to 3 were fabricated using the above-described compounds 123, 124, and 127 as light emitting layer materials.

[Example compound]

An organic electroluminescent device of Comparative Example 1 was fabricated using the following Comparative Example Compound X-1 as a light emitting layer material.

[Comparative Example Compound]

The organic electroluminescent devices of Examples 1 to 3 and Comparative Example 1 were formed by forming a first electrode having a thickness of 150 nm with ITO and dopyrazino [2,3-f: 2 ', 3'-h] quinoxaline-2,3,6 , 7,10,11-hexacarbonitrile (HAT-CN) to form a hole injection layer with a thickness of 10 nm, and the hole injection layer was formed by using N, N'-di (naphthalene-1-yl) -N, N'-diphenyl- A hole transport layer having a thickness of 80 nm was formed, an electron blocking layer having a thickness of 5 nm was formed with mCP, and 18% doping of the compound of Example or Comparative Example with (bis {2- [di (phenyl) phosphino] phenyl} ether oxide (DPEPO) A hole blocking layer having a thickness of 10 nm was formed with (bis {2- [di (phenyl) phosphino] phenyl} ether oxide (DPEPO), and 1,3,5- 1H-benzimidazol-2-yl) benzene (TPBi) to form an electron transporting layer having a thickness of 30 nm, an electron injecting layer having a thickness of 0.5 nm with lithium fluoride (LiF) and a second electrode having a thickness of 100 nm . Each layer and the second electrode were subjected to a resistance heating method using a vacuum evaporator It was formed.

Next, the maximum emission wavelength, delayed fluorescence lifetime, external quantum efficiency and roll-off of the fabricated organic electroluminescent device were evaluated. The evaluation results are shown in Table 1 below. The maximum emission wavelength was the maximum emission wavelength of the emission spectrum at room temperature (about 300K). The external quantum efficiency was measured using a C9920-12 apparatus from Hamamatsu photonics.

Device fabrication The light- lambda max Delayed fluorescence lifetime
(?? s) Roll-off ^{1 )}
(%) Example 1 Example Compound 123 460 100 0.68 Example 2 Example Compound 124 450 125 0.65 Example 3 Example Compound 127 440 100 0.75 Comparative Example 1 Comparative Example Compound X-1 450 900 0.2

1) Roll-off = EQE (cd / 10mA) / EQE (max)

From the results of Table 1, it can be seen that the aromatic compound according to an embodiment of the present invention is a thermally active delayed fluorescence (TADF) material exhibiting blue light emission of 470 nm or less. Comparing Examples 1 to 3 and Comparative Example 1, it can be seen that the aromatic compound according to one embodiment of the present invention has a short delayed fluorescence lifetime and a reduced roll-off. As a result, the introduction of a linker having a large steric hindrance has been suggested to reduce the roll-off due to the renormalization. Particularly, in the case of a compound having a large spin-orbit coupling and a large stereoscopic effect as in Example 1, the above effect is maximized.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It will be understood. It is therefore to be understood that the above-described embodiments are illustrative and non-restrictive in every respect.

10: organic electroluminescence device EL1: first electrode
HTR: hole transport region EML: light emitting layer
ETR: Electron transporting region EL2: Second electrode

Claims (19)

An aromatic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R ₁ to R ₄ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming 2 Or more and 30 or less,
At least two of R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted ring- A heteroaryl group having 2 or more and 30 or less,
A is represented by any one of the following formulas (2-1) to (2-11)
[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Chemical Formula 2-4] [Chemical Formula 2-5]

[Chemical Formula 2-6] [Chemical Formula 2-7]

[Chemical Formula 2-8] [Chemical Formula 2-9]

[Chemical Formula 2-10] [Chemical Formula 2-11]

In the above Chemical Formulas 2-1 to 2-11,
Q ₁ to Q ₁₅ each independently represent a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming carbon number of 2 to 30 Lt; / RTI >
a, d, e, f, g, m, n and o are each independently an integer of 0 to 4,
b, c, h, i, j, k and l are each independently an integer of 0 to 3,
In Formula 1,
D is represented by the following formula 3-1 or 3-2:
[Formula 3-1] [Formula 3-2]

In the above Formulas (3-1) and (3-2)
L ₁ and L ₂ each independently represent a direct linkage or a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms,
R ₅ to R ₂₂ each independently represent a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 to 30 Or a substituted or unsubstituted heteroaryl group having a ring-forming carbon number of 2 to 30,
X is CRaRb, SiRcRd, GeReRf, NRg, O or S,
Ra to Rg each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
Ra and Rb, Rc and Rd, and Re and Rf may combine with each other to form a ring. The method according to claim 1,
The aromatic compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-4)
[Formula 1-1] [Formula 1-2]

[Chemical Formula 1-3] [Chemical Formula 1-4]

In the above Formulas 1-1 to 1-4,
R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted ring-forming carbon number of 2 to 30 Lt; / RTI >
A and D are the same as defined in claim 1. The method according to claim 1,
At least two of R ₁ to R ₄ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl-containing group having 6 to 30 ring-forming carbon atoms. The method according to claim 1,
And at least two of R ₁ to R ₄ are each independently a methyl group or a phenyl group. The method according to claim 1,
D is represented by the above formula (3-2), X is CRaRb, and Ra and Rb are the same as defined in claim 1. The method according to claim 1,
D is an aromatic compound represented by any one of the following formulas (3-2-1) to (3-2-5):
[Formula 3-2-1] [Formula 3-2-2]

[Formula 3-2-3] [Formula 3-2-4]

[Chemical Formula 3-2-5]

.
In the above formulas (3-2-1) to (3-2-5)
L ₂ , R ₁₅ to R ₁₇ and R ₂₀ to R ₂₂ are the same as defined in claim 1. The method according to claim 1,
L ₁ and L ₂ are each independently a direct bond. The method according to claim 1,
Wherein the aromatic compound represented by Formula 1 is at least one selected from the compounds represented by the following Group 1:
[Compound group 1]

. A first electrode;
A hole transporting region provided on the first electrode;
A light emitting layer provided on the hole transporting region;
An electron transporting region provided on the light emitting layer; And
And a second electrode provided on the electron transporting region,
Wherein at least one of the hole transporting region, the light emitting layer and the electron transporting region comprises an aromatic compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
R ₁ to R ₄ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming 2 Or more and 30 or less,
At least two of R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted ring- A heteroaryl group having 2 or more and 30 or less,
A is represented by any one of the following formulas (2-1) to (2-11)
[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Chemical Formula 2-4] [Chemical Formula 2-5]

[Chemical Formula 2-6] [Chemical Formula 2-7]

[Chemical Formula 2-8] [Chemical Formula 2-9]

[Chemical Formula 2-10] [Chemical Formula 2-11]

In the above Chemical Formulas 2-1 to 2-11,
Q ₁ to Q ₁₅ each independently represent a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming carbon number of 2 to 30 Lt; / RTI >
a, d, e, f, g, m, n and o are each independently an integer of 0 to 4,
b, c, h, i, j, k and l are each independently an integer of 0 to 3,
In Formula 1,
D is represented by the following formula 3-1 or 3-2:
[Formula 3-1] [Formula 3-2]

In the above Formulas (3-1) and (3-2)
L ₁ and L ₂ each independently represent a direct linkage or a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms,
R ₅ to R ₂₂ each independently represent a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 to 30 Or a substituted or unsubstituted heteroaryl group having a ring-forming carbon number of 2 to 30,
X is CRaRb, SiRcRd, GeReRf, NRg, O or S,
Ra to Rg each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
Ra and Rb, Rc and Rd, and Re and Rf may combine with each other to form a ring. 10. The method of claim 9,
Wherein the light emitting layer comprises an aromatic compound represented by Formula 1. 10. The method of claim 9,
The aromatic compound represented by the formula (1)
Wherein an absolute value of a singlet energy level and a triplet energy level difference is 0.2 eV or less. 10. The method of claim 9,
The aromatic compound represented by the formula (1)
Wherein the material is a thermally active delayed fluorescent light emitting material. 10. The method of claim 9,
(1) is represented by any one of the following formulas (1-1) to (1-4):
[Formula 1-1] [Formula 1-2]

[Chemical Formula 1-3] [Chemical Formula 1-4]

In the above Formulas 1-1 to 1-4,
R ₁ to R ₄ each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted ring-forming carbon number of 2 to 30 Lt; / RTI >
A and D are the same as defined in claim 9. 10. The method of claim 9,
At least two of R ₁ to R ₄ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. 10. The method of claim 9,
And at least two of R ₁ to R ₄ are each independently a methyl group or a phenyl group. 10. The method of claim 9,
D is represented by the above formula (3-2), X is CRaRb, and Ra and Rb are the same as defined in claim 1. 10. The method of claim 9,
D is represented by any one of the following formulas (3-2-1) to (3-2-5):
[Formula 3-2-1] [Formula 3-2-2]

[Formula 3-2-3] [Formula 3-2-4]

[Chemical Formula 3-2-5]

In the above formulas (3-2-1) to (3-2-5)
L ₂ , R ₁₅ to R _17, and R ₂₀ to R ₂₂ are the same as defined in claim 9. 10. The method of claim 9,
L ₁ and L ₂ are each independently a direct bond. 10. The method of claim 9,
Wherein the aromatic compound represented by Formula 1 is at least one selected from the compounds represented by the following Group 1:
[Compound group 1]

.

Images