KR20210127361A - Heterocyclic compound and organic light emitting device including the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device including the same. The heterocyclic compound described herein can be used as an organic material layer of the organic light emitting device. The heterocyclic compound can serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device.

Description

Heterocyclic compound and organic light emitting device comprising the same

The present specification relates to a heterocyclic compound and an organic light emitting device including the same.

The electroluminescent device is a type of self-luminous display device, and has a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan, or efficiency of the organic light emitting device, the development of a material for the organic thin film is continuously required.

U.S. Patent No. 4,356,429

An object of the present specification is to provide a heterocyclic compound and an organic light emitting device including the same.

In one embodiment of the present specification, there is provided a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each independently N or CR _A , and at least two are N,

R _A and R ₁ are hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

D _A and D _B are each independently represented by the following formula (2),

[Formula 2]

In Formula 2,

Y is a direct bond; O; S; NR _B ; or CR _C R _D ,

R ₁₁ to R ₁₈ , and R _B to R _D are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Groups of adjacent R ₁₁ to R _18, and R _B to R _D may form a substituted or unsubstituted ring by combining to each other,

는 상기 화학식 1과 결합되는 위치이다.

is a position bonded to Formula 1 above.

In addition, according to an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes at least one heterocyclic compound represented by Formula 1 above.

The heterocyclic compound described herein may be used as an organic material layer material of an organic light emitting device. The heterocyclic compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device. In particular, the heterocyclic compound may be used as a light emitting layer material of an organic light emitting device.

In the heterocyclic compound, the electron cloud distribution of HOMO and LUMO is further separated as the dihedral angle increases as Donor, Acceptor, and Donor-C are substituted at ortho positions with each other, and through this, ΔE _ST (S ₁ -T ₁ ) TADF (Thermally Activated Delayed Fluorence) characteristics are improved by decreasing the value, and as a result, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifespan characteristics of the device can be improved.

1 to 3 are diagrams exemplarily showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.

는 치환되는 위치를 의미한다.In this specification,

means a position to be substituted.

In the present specification, "substituted or unsubstituted" refers to a C1 to C60 straight-chain or branched alkyl group; C2 to C60 linear or branched alkenyl group; C2 to C60 linear or branched alkynyl group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heteroaryl group; silyl group; phosphine oxide group; And it means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an amine group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected.

In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

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

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

In the present specification, the aryl group includes a monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by _{-SiR 104} R ₁₀₅ R _{106 , R 104} to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specific 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, a phenylsilyl group, and the like. It is not limited.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes O, S, SO ₂ Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthridyl group Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, benzofuro[2,3-d]pyrimidyl group; benzothieno[2,3-d] pyrimidyl group; Benzofuro[2,3-a]carbazolyl group, benzothieno[2,3-a]carbazolyl group, 1,3-dihydroindolo[2,3-a]carbazolyl group, benzofuro [3,2-a] carbazolyl group, benzothieno [3,2-a] carbazolyl group, 1,3-dihydroindolo [3,2-a] carbazolyl group, benzofuro [2, 3-b] carbazolyl group, benzothieno [2,3-b] carbazolyl group, 1,3-dihydroindolo [2,3-b] carbazolyl group, benzofuro [3,2-b ]carbazolyl group, benzothieno[3,2-b]carbazolyl group, 1,3-dihydroindolo[3,2-b]carbazolyl group, benzofuro[2,3-c]carbazolyl group Group, benzothieno[2,3-c]carbazolyl group, 1,3-dihydroindolo[2,3-c]carbazolyl group, benzofuro[3,2-c]carbazolyl group, benzo Thieno [3,2-c] carbazolyl group, 1,3-dihydroindolo [3,2-c] carbazolyl group, 1,3-dihydroindeno [2,1-b] carbazolyl group , 5,11-dihydroindeno [1,2-b] carbazolyl group, 5,12-dihydroindeno [1,2-c] carbazolyl group, 5,8-dihydroindeno [2, 1-c] carbazolyl group, 7,12-dihydroindeno[1,2-a]carbazolyl group, 11,12-dihydroindeno[2,1-a]carbazolyl group, and the like. , but is not limited thereto.

In the present specification, the phosphine oxide group may be specifically substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethyl phosphine oxide group, a diphenyl phosphine oxide group, and a dinaphthyl phosphine oxide group.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, examples of the aryl group described above may be applied to the arylene group, except that the arylene group is a divalent group.

In the present specification, the heteroarylene group, except that the heteroarylene group is a divalent group, examples of the above-described heteroaryl group may be applied.

In the present specification, "adjacent group" refers to a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can mean For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent groups".

The structures exemplified by the above-described cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group may be applied, except that the aliphatic or aromatic hydrocarbon ring or aliphatic or aromatic heterocycle that adjacent groups may form is not a monovalent group.

In an exemplary embodiment of the present specification, a heterocyclic compound represented by Formula 1 is provided.

As D _A and D _B, which act as electron donors, are substituted in the ortho position between the cyano group and triazine (or pyrimidine) acting as electron acceptors, respectively, the separation of HOMO and LUMO becomes smooth as the dihedral angle increases, so TADF (Thermal activated delayed fluorescence, Thermally Activated Delayed Fluorence) properties are improved.

The TADF causes a reverse intersystem transition from T ₁ (triplet energy level) to S ₁ (singlet energy level) due to thermal energy, and then fluorescence occurs from S _{1 to S 0} (singlet ground state). The step of inverse transition is more necessary than the fluorescence phenomenon, and the _{smaller the difference between T 1 and S 1} , the easier the reverse transition can occur. There is an effect that the difference between ₁ and S _{1 values becomes smaller.}

That is, in the compound of Formula 1, HOMO and LUMO separation is facilitated, so that ΔE _ST decreases, and TADF characteristics are improved, thereby improving device characteristics.

In the present specification, ΔE _ST means _{the difference (S 1} -T ₁ ) _{between S 1} (singlet energy level) and T ₁ (triplet energy level).

_{ΔE ST} (S ₁ -T ₁ ) of the heterocyclic compound according to an exemplary embodiment of the present specification is 0.3 or less. Specifically, it is 0.01 or more and 0.3 or less, or 0.01 or more and 0.25 or less.

_{S 1} (singlet energy level) of the heterocyclic compound according to an exemplary embodiment of the present specification is 2.4 to 2.8.

_{T 1} (triplet energy level) of the heterocyclic compound according to an exemplary embodiment of the present specification is 2.1 to 2.75.

The singlet energy level and the triplet energy level may be measured using a method known in the art, but is not limited thereto.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, the definition of each substituent is the same as the definition in Formula 1.

In an exemplary embodiment of the present specification, R ₁ is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ is a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ is a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ is a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; Or it may be a substituted or unsubstituted pyridine group.

In an exemplary embodiment of the present specification, R ₁ is a methyl group; phenyl group; biphenyl group; or a pyridine group.

In an exemplary embodiment of the present specification, D _A and D _B are each independently represented by Formula 2 below.

[Formula 2]

In Formula 2,

Y is a direct bond; O; S; NR _B ; or CR _C R _D ,

R ₁₁ to R ₁₈ , and R _B to R _D are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Groups of adjacent R ₁₁ to R _18, and R _B to R _D may form a substituted or unsubstituted ring by combining to each other,

는 상기 화학식 1과 결합되는 위치이다.

is a position bonded to Formula 1 above.

In an exemplary embodiment of the present specification, Y may be a direct bond.

In an exemplary embodiment of the present specification, Y may be O.

In an exemplary embodiment of the present specification, Y may be S.

In an exemplary embodiment of the present specification, Y is NR _B , R _B is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, Y is CR _C R _D , R _C and R _D are each independently, a substituted or unsubstituted C1 to C10 alkyl group; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In the exemplary embodiment of the present specification, Y is CR _C R _D , and R _C and R _D may be bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R ₁₁ to R ₁₈ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group, and _{adjacent groups of R 11} to R ₁₈ may be bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R ₁₁ to R ₁₈ are each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.

In an exemplary embodiment of the present specification, R ₁₁ to R ₁₈ are each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present specification, R ₁₁ to R ₁₈ are each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R ₁₁ to R ₁₈ are each independently hydrogen; heavy hydrogen; or a phenyl group.

In the exemplary embodiment of the present specification, _{adjacent groups of R 11} to R _{18 may} combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, _{adjacent groups of R 11} to R ₁₈ are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; Or it may form a substituted or unsubstituted aromatic heterocycle.

In an exemplary embodiment of the present specification, R ₁₁ and R ₁₂ may be bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R ₁₂ and R ₁₃ may be combined with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R ₁₃ and R ₁₄ may be combined with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Chemical Formula 2 may be represented by any one of Chemical Formulas 2-1 to 2-6 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,

Y ₁ is O; S; NR _E ; or CR _F R _G ,

Z is O; S; NR _H ; or CR _I R _J ,

R _E to R _J and R ₂₁ to R ₂₄ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r21 and r24 are each an integer from 1 to 8,

r22 and r23 are each an integer from 1 to 10,

When each of r21 to r24 is 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, R ₂₁ is hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.

In an exemplary embodiment of the present specification, R ₂₁ is hydrogen; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present specification, R ₂₁ is hydrogen; Or it may be a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R ₂₂ to R ₂₄ may be hydrogen.

In an exemplary embodiment of the present specification, Z may be O.

In one embodiment of the present specification, Z may be S.

In an exemplary embodiment of the present specification, Z is NR _H , and R _H may be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present specification, Z is NR _H , and R _H may be a substituted or unsubstituted C6 to C30 aryl group.

In the exemplary embodiment of the present specification, Z is CR _I R _J , and R _I and R _J may each independently be a substituted or unsubstituted C1 to C10 alkyl group.

In an exemplary embodiment of the present specification, Y ₁ may be O.

In an exemplary embodiment of the present specification, Y ₁ may be S.

In an exemplary embodiment of the present specification, Y ₁ is NR _E , R _E is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, Y ₁ is CR _F R _G , and R _F and R _G are each independently, a substituted or unsubstituted C1 to C10 alkyl group; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

An organic light emitting diode according to an exemplary embodiment of the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes at least one heterocyclic compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, at least one layer of the organic material layer includes one type of heterocyclic compound represented by Formula 1 above.

The organic light emitting device according to an exemplary embodiment of the present specification includes at least one organic material layer, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 above.

The organic light emitting device according to an exemplary embodiment of the present specification includes at least one organic material layer, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1 as a TADF light emitting material.

The organic light emitting device according to an exemplary embodiment of the present specification may further include a host material and a dopant material in the light emitting layer including the heterocyclic compound represented by Formula 1 above.

The organic light emitting device according to an exemplary embodiment of the present specification includes at least one organic material layer, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Formula 1, a host material, and a dopant material.

When the TADF light-emitting material of Formula 1, the host material, and the dopant material are used together in the light-emitting layer of the organic light-emitting device, the half-width of the light-emitting wavelength is lowered and the roll-off phenomenon is also reduced, so that the organic light-emitting device has high light-emitting efficiency. The overall stability is improved and it has a high lifespan.

In the exemplary embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

In another exemplary embodiment of the present specification, the first electrode may be a negative electrode, and the second electrode may be an anode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a blue organic light emitting device, and the compound represented by Formula 1 may be used as a material of the blue organic light emitting device. For example, the compound represented by Formula 1 may be included in the light emitting layer of the blue organic light emitting device.

In the exemplary embodiment of the present specification, the organic light emitting device may be a green organic light emitting device, and the compound represented by Formula 1 may be used as a material of the green organic light emitting device. For example, the compound represented by Formula 1 may be included in the emission layer of the green organic light emitting diode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a red organic light emitting device, and the compound represented by Formula 1 may be used as a material of the red organic light emitting device. For example, the compound represented by Formula 1 may be included in the emission layer of the red organic light emitting device.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an 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.

The organic light emitting device of the present invention may further include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

Referring to FIG. 1 , an organic light emitting device in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially stacked on a substrate 100 is illustrated. However, it is not limited to such a structure, and as shown in FIG. 2 , an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case in which the organic material layer is multi-layered. The organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic material layer including the heterocyclic compound represented by Formula 1 may further include other materials if necessary.

In the organic light emitting device according to an exemplary embodiment of the present specification, materials other than the heterocyclic compound represented by Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, Materials known in the art may be substituted.

Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO _{2 :Sb;} conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

A red, green or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as separate sources, or may be premixed and deposited as a single source. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material together participate in light emission may be used.

When mixing and using the host of the light emitting material, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of n-type host material or p-type host material may be selected and used as the host material of the light emitting layer.

The organic light emitting device according to the exemplary embodiment of the present specification may be a top emission type, a back emission type, or a double side emission type according to a material used.

The compound according to an exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

[Preparation Example 1] Synthesis of A-1-1

1) Synthesis of intermediate P1

10 g (0.044 mol, 1eq) of intermediate P2 (2,4-dichloro-6-phenyl-1,3,5-triazine) and (3-cyano-2-fluorophenyl) boronic acid in a dehydrated round-bottom flask ((3-cyano-2-fluorophenyl)boronic acid) 17.5 g (0.106 mol 2.4 eq), Pd (PPh ₃ ) ₄ (tetrakis (triphenylphosphine) palladium (0)) 5.1 g (0.00442 mol 10 mol%) , K ₂ CO ₃ 30.5g (0.022mol, 5eq) was added, THF (tetrahydrofuran) 220ml and H ₂ O 40ml were added and stirred at 70°C. After confirming that the reaction was completed by TLC, after cooling to room temperature, 300 ml of EA (ethyl acetate) and _{100 ml of H 2} O were added, and the resulting water layer was extracted once more with MC (methylene chloride) and water was removed with _{MgSO 4 .} Toluene (toluene) 50ml and MeOH (methanol) 300ml were added, the slurry was filtered, and 5g of intermediate P1 was obtained. (yield: 29%, white solid)

2) Synthesis of compound A-1-1

5g (0.0126mol, 1eq) of Intermediate P1(3,3'-(6-phenyl-1,3,5-triazine-2,4-diyl)bis(2-fluorobenzonitrile)) and Intermediate in a dehydrated round-bottom flask C1(9H-carbazole) 4.9g (0.029mol 2.3eq), CS ₂ CO ₃ 20g (0.0632mol 5eq), and DMA (dimethylacetamide) 70ml were added and stirred under reflux. After confirming the reaction by TLC, it was cooled to room temperature and filtered to remove the base. Column (MC:Hex (volume ratio) = 3:2 → 2:1) was separated to obtain 4.3 g of Compound A-1-1. (yield: 49%, green solid)

Compounds A-1-2 to A-1-30 were synthesized in the same manner as in Preparation Example 1, except that an alternative compound described in Table 1 was used instead of Intermediate C1.

Compound No. alternative compound transference number Compound No. alternative compound transference number A-1-1

49% A-1-2

52% A-1-8

45% A-1-11

42% A-1-14

51% A-1-17

42% A-1-21

53% A-1-22

47% A-1-23

57% A-1-25

51% A-1-29

41% A-1-30

47%

Compound A-2-1 to Compound A-6-30 were synthesized in the same manner as Compound A-1-1 to Compound A-1-30, except that the replacement compound described in Table 2 was used instead of Intermediate P2. .

compound
No. alternative compound transference number compound
No. alternative compound transference number A-2-1

43% A-3-1

50% A-4-1

52% A-5-1

46% A-6-1

40%

Compound B-1-1 to Compound B-6-30 were synthesized in the same manner as Compound A-1-1 to Compound A-6-30, except that an alternative compound described in Table 3 was used instead of Intermediate P2. .

compound
No. alternative compound transference number compound
No. alternative compound transference number B-1-1

53% B-2-1

48% B-3-1

55% B-4-1

51% B-5-1

48% B-6-1

49%

The compound was prepared in the same manner as in Preparation Example, and the synthesis confirmation results are shown in Tables 4 and 5. Table 4 is a measurement value of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), Table 5 is a measurement value of ¹ H NMR (CDCl ₃ , 200Mz).

compound FD-MS compound FD-MS A-1-1 m/z=689.23
(C ₄₇ H ₂₇ N ₇ =689.76) A-1-2 m/z=789.26
(C ₅₅ H ₃₁ N ₇ =789.88) A-1-8 m/z=869.25
(C ₅₉ H ₃₁ N ₇ O ₂ =869.92) A-1-14 m/z=921.36
(C ₆₅ H ₄₃ N ₇ =922.08) A-1-17 m/z=1019.35
(C ₇₁ H ₄₁ N ₉ =1020.15) A-1-29 m/z=1017.36
(C ₇₃ H ₄₃ N ₇ =1018.17) A-2-1 m/z=627.22
(C ₄₂ H ₂₅ N ₇ =627.69) A-2-2 m/z=727.25
(C ₅₀ H ₂₉ N ₇ =727.81) A-2-8 m/z=807.24
(C ₅₄ H ₂₉ N ₇ O ₂ =807.85) A-2-14 m/z=859.34
(C ₆₀ H ₄₁ N ₇ =860.01) A-2-17 m/z=957.33
(C ₆₆ H ₃₉ N ₉ =958.08) A-2-29 m/z=955.34
(C ₆₈ H ₄₁ N ₇ =956.10) A-3-1 m/z=765.26
(C ₅₃ H ₃₁ N ₇ =765.86) A-3-2 m/z=865.30
(C ₆₁ H ₃₅ N ₇ =865.98) A-3-8 m/z=945.29
(C ₆₅ H ₃₅ N ₇ O ₂ =946.02) A-3-14 m/z=997.39
(C ₇₁ H ₄₇ N ₇ =998.18) A-3-17 m/z=1095.38
(C ₇₇ H ₄₅ N ₉ =1096.24) A-3-29 m/z=1093.39
(C ₇₉ H ₄₇ N ₇ =1094.27) A-4-1 m/z=690.23
(C ₄₆ H ₂₆ N ₈ =690.75) A-4-2 m/z=790.26
(C ₅₄ H ₃₀ N ₈ =790.87) A-4-8 m/z=870.25
(C ₅₈ H ₃₀ N ₈ O ₂ =870.91) A-4-14 m/z=922.35
(C ₆₄ H ₄₂ N ₈ =923.07) A-4-17 m/z=1020.34
(C ₇₀ H ₄₀ N ₁₀ =1021.13) A-4-29 m/z=1018.35
(C ₇₂ H ₄₂ N ₈ =1019.16) A-5-1 m/z=690.23
(C ₄₆ H ₂₆ N ₈ =690.75) A-5-2 m/z=790.26
(C ₅₄ H ₃₀ N ₈ =790.87) A-5-8 m/z=870.25
(C ₅₈ H ₃₀ N ₈ O ₂ =870.91) A-5-14 m/z=922.35
(C ₆₄ H ₄₂ N ₈ =923.07) A-5-17 m/z=1020.34
(C ₇₀ H ₄₀ N ₁₀ =1021.13) A-5-29 m/z=1018.35
(C ₇₂ H ₄₂ N ₈ =1019.16) A-6-1 m/z=690.23
(C ₄₆ H ₂₆ N ₈ =690.75) A-6-2 m/z=790.26
(C ₅₄ H ₃₀ N ₈ =790.87) A-6-8 m/z=870.25
(C ₅₈ H ₃₀ N ₈ O ₂ =870.91) A-6-14 m/z=922.35
(C ₆₄ H ₄₂ N ₈ =923.07) A-6-17 m/z=1020.34
(C ₇₀ H ₄₀ N ₁₀ =1021.13) A-6-29 m/z=1018.35
(C ₇₂ H ₄₂ N ₈ =1019.16) B-1-1 m/z=688.24
(C ₄₈ H ₂₈ N ₆ =688.78) B-1-2 m/z=788.27
(C ₅₆ H ₃₂ N ₆ =788.89) B-1-8 m/z=868.26
(C ₆₀ H ₃₂ N ₆ O ₂ =868.94) B-1-14 m/z=920.36
(C ₆₆ H ₄₄ N ₆ =921.10) B-1-17 m/z=1018.35
(C ₇₂ H ₄₂ N ₈ =1019.16) B-1-29 m/z=1016.36
(C ₇₄ H ₄₄ N ₆ =1017.18) B-2-1 m/z=626.22
(C ₄₃ H ₂₆ N ₆ =626.71) B-2-2 m/z=726.25
(C ₅₁ H ₃₀ N ₆ =726.82) B-2-8 m/z=806.24
(C ₅₅ H ₃₀ N ₆ O ₂ =806.87) B-2-14 m/z=858.35
(C ₆₁ H ₄₂ N ₆ =859.03) B-2-17 m/z=956.34
(C ₆₇ H ₄₀ N ₈ =957.09) B-2-29 m/z=954.35
(C ₆₉ H ₄₂ N ₆ =955.11) B-3-1 m/z=764.27
(C ₅₄ H ₃₂ N ₆ =764.87) B-3-2 m/z=864.30
(C ₆₂ H ₃₆ N ₆ =864.99) B-3-8 m/z=944.29
(C ₆₆ H ₃₆ N ₆ O ₂ =945.03) B-3-14 m/z=996.39
(C ₇₂ H ₄₈ N ₆ =997.19) B-3-17 m/z=1094.38
(C ₇₈ H ₄₆ N ₈ =1095.25) B-3-29 m/z=1092.39
(C ₈₀ H ₄₈ N ₆ =1093.28) B-4-1 m/z=689.23
(C ₄₇ H ₂₇ N ₇ =689.76) B-4-2 m/z=789.26
(C ₅₅ H ₃₁ N ₇ =789.88) B-4-8 m/z=869.25
(C ₅₉ H ₃₁ N ₇ O ₂ =869.92) B-4-14 m/z=921.36
(C ₆₅ H ₄₃ N ₇ =922.08) B-4-17 m/z=1019.35
(C ₇₁ H ₄₁ N ₉ =1020.15) B-4-29 m/z=1017.36
(C ₇₃ H ₄₃ N ₇ =1018.17) B-5-1 m/z=689.23
(C ₄₇ H ₂₇ N ₇ =689.76) B-5-2 m/z=789.26
(C ₅₅ H ₃₁ N ₇ =789.88) B-5-8 m/z=869.25
(C ₅₉ H ₃₁ N ₇ O ₂ =869.92) B-5-14 m/z=921.36
(C ₆₅ H ₄₃ N ₇ =922.08) B-5-17 m/z=1019.35
(C ₇₁ H ₄₁ N ₉ =1020.15) B-5-29 m/z=1017.36
(C ₇₃ H ₄₃ N ₇ =1018.17) B-6-1 m/z=689.23
(C ₄₇ H ₂₇ N ₇ =689.76) B-6-2 m/z=789.26
(C ₅₅ H ₃₁ N ₇ =789.88) B-6-8 m/z=869.25
(C ₅₉ H ₃₁ N ₇ O ₂ =869.92) B-6-14 m/z=921.36
(C ₆₅ H ₄₃ N ₇ =922.08) B-6-17 m/z=1019.35
(C ₇₁ H ₄₁ N ₉ =1020.15) B-6-29 m/z=1017.36
(C ₇₃ H ₄₃ N ₇ =1018.17)

compound ^One H NMR (CDCl ₃ , 200 Mz) A-1-1 δ = 8.55 (2H, d), 8.28 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.25 (17H, d) A-1-2 δ = 8.55 (2H, d), 8.28 (2H, d), 8.16 to 8.07 (6H, m), 7.94 (2H, d), 7.69 to 7.51 (12H, d), 7.41 to 7.25 (7H, m) A-1-8 δ = 8.55 (2H, d), 8.28 (2H, d), 8.07 (2H, d), 7.94 to 7.89 (4H, m), 7.69 to 7.32 (21H, m), 7.41 to 7.25 (7H, m) A-1-14 δ = 8.55 (2H, d), 8.28 (2H, d), 8.09-8.07 (4H, m), 7.94 (2H, d), 7.69-7.60 (8H, d), 7.51-7.24 (13H, m), 1.72 (12H, s) A-1-17 δ = 8.55 (4H, d), 8.28 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.23 (27H, d), 7.41 to 7.25 (7H, m) A-1-29 δ = 8.28 (2H, d), 7.87~7.82 (6H, d), 7.55~7.51 (6H, m), 7.41~7.28 (11H, m), 7.05~6.98 (10H, m), 6.69 (4H, m) ), 6.51 (4H, m) A-2-1 δ = 8.55 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.50 (8H, m), 7.33 to 7.25 (6H, m), 2.44 (3H, s) A-2-2 δ = 8.55 (2H, d), 8.16 to 8.07 (6H, m), 7.94 (2H, d), 7.69 to 7.55 (10H, m), 7.33 to 7.25 (6H, m), 2.44 (3H, s) A-2-8 δ = 8.55 (2H, d), 8.07 (2H, m), 7.94 to 7.89 (4H, m), 7.69 to 7.60 (6H, m), 7.49 to 7.32 (12H, m), 2.44 (3H, s) A-2-14 δ = 8.55 (2H, d), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.60 (8H, m), 7.44 (2H, m), 7.33 to 7.24 (8H, m), 2.44 (3H, s), 1.72 (12H, s) A-2-17 δ = 8.55 (4H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.45 (14H, m), 7.33 to 7.23 (10H, m), 2.44 (3H, s) A-2-29 δ = 7.87~7.82 (6H, m), 7.55 (4H, d), 7.38~7.28 (10H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d), 2.44 (3H, s) A-3-1 δ = 8.55 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.85 (2H, d), 7.69 to 7.25 (21H, d) A-3-2 δ = 8.55 (2H, d), 8.16~8.07 (6H, m), 7.94 (2H, d), 7.85 (2H, d), 7.69~7.25 (23H, d) A-3-8 δ = 8.55 (2H, d), 8.07 (2H, d), 7.94 to 7.85 (6H, m), 7.69 to 7.25 (25H, m) A-3-14 δ = 8.55 (2H, d), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.85 (2H, d), 7.69 to 7.60 (8H, d), 7.52 to 7.24 (17H, m), 1.72 (12H, s) A-3-17 δ = 8.55 (4H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.85 (2H, d), 7.69 (2H, m), 7.58 to 7.25 (29H, m) A-3-29 δ = 7.87~7.82 (8H, m), 7.55~7.25 (21H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, m) A-4-1 δ = 8.59~8.55 (3H, m), 8.38 (1H, d), 8.12~8.07 (4H, m), 7.94~7.85 (3H, m), 7.69~7.50 (8H, m), 7.36~7.25 (7H) , m) A-4-2 δ = 8.59~8.55 (3H, m), 8.38 (1H, d), 8.16~8.07 (6H, m), 7.94 (2H, d), 7.85 (1H, t), 7.69~7.55 (10H, m), 7.40~7.25 (7H, m) A-4-8 δ = 8.59~8.55 (3H, m), 8.38 (1H, d), 8.07 (2H, d), 7.94~7.85 (5H, m), 7.69~7.60 (6H, m), 7.49 (2H, s), 7.42~7.25 (11H, m) A-4-14 δ = 8.59~8.55 (3H, m), 8.38 (1H, d), 8.09~8.07 (4H, m), 7.94 (2H, d), 7.85 (1H, t), 7.69~7.60 (8H, m), 7.44~7.24 (11H, m) 1.72 (12H, s) A-4-17 δ = 8.59~8.55 (5H, m), 8.38 (1H, d), 8.12~8.07 (4H, m), 7.94~7.85 (5H, m), 7.69~7.25 (25H, m) A-4-29 δ = 8.59 (1H, d), 8.38 (1H, d), 7.87 to 7.82 (7H, m), 7.55 (4H, d), 7.36 to 7.28 (11H, m), 7.05 to 6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d) A-5-1 δ = 9.24 (1H, s), 8.70 (1H, d), 8.55 (2H, d), 8.42 (1H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.50 ( 9H, m), 7.33~7.25 (6H, m) A-5-2 δ = 9.24 (1H, s), 8.70 (1H, d), 8.55 (2H, d), 8.42 (1H, d), 8.16 to 8.07 (6H, m), 7.94 (2H, d), 7.69 to 7.55 ( 11H, m), 7.40~7.25 (6H, m) A-5-8 δ = 9.24 (1H, s), 8.70 (1H, d), 8.55 (2H, d), 8.42 (1H, d), 8.07 (2H, d), 7.94 to 7.89 (4H, m), 7.69 to 7.25 ( 19H, m) A-5-14 δ = 9.24 (1H, s), 8.70 (1H, d), 8.55 (2H, d), 8.42 (1H, d), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.57 ( 9H, m), 7.44 (2H, m), 7.33~7.24 (8H, m), 1.72 (12H, s) A-5-17 δ = 9.24 (1H, s), 8.70 (1H, d), 8.55 (4H, d), 8.42 (1H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.45 ( 15H, m), 7.33~7.23 (10H, m) A-5-29 δ = 9.24 (1H, s), 8.70 (1H, d), 8.42 (1H, d), 7.87 to 7.82 (6H, m), 7.57 to 7.55 (5H, m), 7.38 to 7.28 (10H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d) A-6-1 δ = 8.75 (2H, d), 8.55 (2H, d), 8.25 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.50 (8H, m), 7.36 to 7.25 (6H, m) A-6-2 δ = 8.75 (2H, d), 8.55 (2H, d), 8.25 to 8.07 (8H, m), 7.94 (2H, d), 7.69 to 7.55 (10H, m), 7.40 to 7.25 (6H, m) A-6-8 δ = 8.75 (2H, d), 8.55 (2H, d), 8.25 (2H, d), 8.07 (2H, m), 7.94 to 7.89 (4H, m), 7.69 to 7.60 (6H, m), 7.49 to 7.25 (12H, m) A-6-14 δ = 8.75 (2H, d), 8.55 (2H, d), 8.25 (2H, d), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.60 (8H, m), 7.44 ( 2H, m), 7.33~7.24 (8H, m), 1.72 (12H, s) A-6-17 δ = 8.75 (2H, d), 8.55 (4H, d), 8.25 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.45 (14H, m), 7.33 to 7.23 (10H, m) A-6-29 δ = 8.75 (2H, d), 8.25 (2H, d), 7.87 to 7.82 (6H, m), 7.55 (4H, d), 7.38 to 7.28 (10H, m), 7.05 to 6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d) B-1-1 δ = 8.55 (2H, d), 8.28~8.23 (3H, m), 8.12~8.07 (4H, m), 7.94(2H, d), 7.69~7.25 (17H, m) B-1-2 δ = 8.55 (2H, d), 8.28 to 8.07 (9H, m), 7.94 (2H, d), 7.69 to 7.51 (12H, m) 7.40 to 7.23 (7H, m) B-1-8 δ = 8.55 (2H, d), 8.28~8.23 (3H, m), 8.07 (2H, d), 7.94~7.89 (4H, m), 7.69~7.25 (21H, m) B-1-14 δ = 8.55 (2H, d), 8.28~8.23 (3H, m), 8.09~8.07 (4H, m), 7.94(2H, d), 7.69~7.60 (8H, m), 7.51~7.24 (13H, m) ), 1.72 (12H, s) B-1-17 δ = 8.55 (4H, d), 8.28~8.23 (3H, m), 8.12~8.07 (4H, m), 7.94(4H, d), 7.69~7.23 (27H, m) B-1-29 δ = 9.11 (2H, d), 8.28-8.23 (3H, m), 7.87 (4H, d), 7.51~7.28 (17H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d) B-2-1 δ = 8.55 (2H, d), 8.39 (1H, s), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.50 (8H, m), 7.33 to 7.25 (6H, m), 2.44 (3H, s) B-2-2 δ = 8.55 (2H, d), 8.39 (1H, s), 8.16 to 8.07 (6H, m), 7.94 (2H, d), 7.69 to 7.555 (10H, m), 7.40 to 7.25 (6H, m), 2.44 (3H, s) B-2-8 δ = 8.55 (2H, d), 8.39 (1H, s), 8.07 (2H, d), 7.94 to 7.89 (4H, m), 7.69 to 7.60 (6H, m), 7.49 to 7.25 (12H, m), 2.44 (3H, s) B-2-14 δ = 8.55 (2H, d), 8.39 (1H, s), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.60 (8H, m), 7.44 (2H, m), 7.33 to 7.24 (8H, m), 2.44 (3H, s), 1.72 (12H, s) B-2-17 δ = 8.55 (4H, d), 8.39 (1H, s), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.50 (14H, m), 7.33 to 7.25 (10H, m), 2.44 (3H, s) B-2-29 δ = 9.11 (2H, d), 8.39 (1H, s), 7.87 (4H, d), 7.55 (4H, m), 7.38~7.28 (10H, m), 6.69 (4H, m), 6.51 (4H, d), 2.44 (3H, s) B-3-1 δ = 8.55 (2H, d), 8.23~8.19 (5H, m), 7.96~7.94 (4H, m), 7.84(2H, d), 7.75~7.68 (4H, m), 7.58~7.35 (9H, m) ), 7.25~7.16 (6H, m) B-3-2 δ = 8.55 (2H, d), 8.28~8.11 (7H, m), 7.96~7.94 (4H, m), 7.84~7.68 (10H, m), 7.55~7.16 (13H, m) B-3-8 δ = 8.55 (2H, d), 8.23~8.19 (3H, m), 7.98~7.94 (6H, m), 7.84(2H, d), 7.75~7.68 (4H, m), 7.54~7.16 (19H, m) ) B-3-14 δ = 8.55 (2H, d), 8.24~8.19 (5H, m), 7.96~7.94 (4H, m), 7.88~7.84(4H, m), 7.75~7.68 (6H, m), 7.57~7.35 (11H) , m), 7.25 (2H, m), 7.16 (2H, m), 1.69 (12H, s) B-3-17 δ = 8.55 (4H, d), 8.19~8.12 (5H, m), 7.96~7.94 (6H, m), 7.84(2H, d), 7.75~7.35 (21H, m), 7.25~7.16 (8H, m) ) B-3-29 δ = 9.20 (2H, d), 8.23 (1H, s), 7.96 to 7.90 (6H, m), 7.75 (2H, d), 7.66 (2H, d), 7.55 to 7.14 (29H, m), 6.95 ( 4H, m), B-4-1 δ = 8.59~8.55 (3H, m), 8.38~8.37 (2H, m), 8.12~8.09 (4H, m), 7.94~7.85 (3H, m), 7.69~7.50 (8H, m), 7.36~7.25 (7H, m) B-4-2 δ = 8.59~8.55 (3H, m), 8.38~8.37 (2H, m), 8.16~8.07 (6H, m), 7.94 (2H, d), 7.85 (1H, t), 7.69~7.55 (10H, m) ), 7.36~7.25 (7H, m) B-4-8 δ = 8.59~8.55 (3H, m), 8.38~8.37 (2H, m), 8.07 (2H, d), 7.94~7.85 (5H, m), 7.69~7.60 (6H, m), 7.49 (2H, s) ), 7.42~7.25 (11H, m) B-4-14 δ = 8.59~8.55 (3H, m), 8.38~8.37 (2H, m), 8.09~8.07 (4H, m), 7.94 (2H, d), 7.85 (1H, t), 7.69~7.60 (8H, m) ), 7.44~7.24 (11H, m), 1.72 (12H, s) B-4-17 δ = 8.59~8.55 (5H, m), 8.38~8.37 (2H, m), 8.12~8.07 (4H, m), 7.94~7.85 (5H, m), 7.69~7.23 (25H, m) B-4-29 δ = 9.11 (2H, s), 8.59 (1H, d), 8.38 to 8.37 (2H, m), 7.87 to 7.85 (5H, m), 7.55 (4H, d), 7.38 to 7.28 (11H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, s) B-5-1 δ = 9.24 (1H, s), 8.73-8.70 (2H, m), 8.55 (2H, d), 8.42 (1H, d), 8.19 (4H, m), 7.94 (2H, d), 7.84 (2H, d), 7.68 (2H, m), 7.58 to 7.50 (5H, m), 7.35 (2H, m), 7.20 to 7.16 (4H, m), B-5-2 δ = 9.24 (1H, s), 8.73 to 8.70 (2H, m), 8.55 (2H, d), 8.42 (1H, d), 8.28 to 8.11 (6H, m), 7.94 (2H, d), 7.84 to 7.68 (8H, m), 7.57~7.55 (3H, m), 7.40~7.35 (4H, m), 7.16 (2H, m), B-5-8 δ = 9.24 (1H, s), 8.73 to 8.70 (2H, m), 8.55 (2H, d), 8.42 (1H, d), 8.19 (2H, m), 7.98 to 7.94 (4H, d), 7.84 ( 2H, d), 7.68 (2H, m), 7.57~7.31 (13H, m), 7.16 (2H, m) B-5-14 δ = 9.24 (1H, s), 8.73 to 8.70 (2H, m), 8.55 (2H, d), 8.42 (1H, d), 8.24 to 8.19 (4H, m), 7.88 to 7.84 (6H, m), 7.74~7.68 (4H, m), 7.57 (3H, m), 7.49 (2H, s), 7.38~7.35 (4H, m), 7.16 (2H, m), 1.69 (12H, s) B-5-17 δ = 9.24 (1H, s), 8.73~8.70 (2H, m), 8.55 (4H, d), 8.42 (1H, m), 8.19~8.12 (4H, m), 7.94 (4H, d), 7.84 ( 2H, d), 7.68~7.50 (13H, m), 7.35 (4H, m), 7.18~7.16 (6H, m) B-5-29 δ = 9.24 to 9.20 (3H, m), 8.73 to 8.70 (2H, m), 8.42 (1H, m), 7.90 (4H, m), 7.66 (2H, m), 7.57 to 7.55 (5H, m), 7.38~7.17 (22H, m), 6.95 (4H, m) B-6-1 δ = 8.75 (2H, d), 8.59 to 8.55 (3H, m), 8.25 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.50 (8H, m), 7.33~7.25 (6H, m), B-6-2 δ = 8.75 (2H, d), 8.59 to 8.55 (3H, m), 8.25 to 8.07 (8H, m), 7.94 (2H, d), 7.69 to 7.55 (10H, m), 7.40 to 7.25 (6H, m) ), B-6-8 δ = 8.75 (2H, d), 8.59~8.55 (3H, m), 8.25 (2H, d), 8.07 (2H, m), 7.94~7.89 (4H, m), 7.69~7.60 (6H, m), 7.49~7.25 (12H, m), B-6-14 δ = 8.75 (2H, d), 8.59 to 8.55 (3H, m), 8.25 (2H, d), 8.09 to 8.07 (4H, m), 7.94 (2H, d), 7.69 to 7.60 (8H, m), 7.44 (2H, m), 7.33~7.24 (8H, m), 1.69 (12H, s) B-6-17 δ = 8.75 (2H, d), 8.59 to 8.55 (5H, m), 8.25 (2H, d), 8.12 to 8.07 (4H, m), 7.94 (4H, d), 7.69 to 7.45 (14H, m), 7.33~7.23 (10H, m), B-6-29 δ = 9.11 (2H, d), 8.75 (2H, d), 8.59 (1H, s), 8.25 (2H, s), 7.87 (4H, d), 7.55 (4H, m), 7.38 to 7.28 (10H, m), 7.05~6.98 (10H, m), 6.69 (4H, m), 6.51 (4H, d)

<Organic EL production and evaluation>

Example 1)

A glass substrate (manufactured by Geomatics) with an ITO (Indium Tin Oxide) transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm. The cleaned glass substrate with transparent electrode line is mounted on the substrate holder of the vacuum deposition apparatus, and the transparent electrode is covered on the side where the transparent electrode line is formed first, so that the compound HAT-CN (dipyrazino[2,3-f:2 ',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) was deposited and a hole injection layer with a thickness of 5 nm was formed.

Next, the compound HT-1 was vapor-deposited on the hole injection layer, and the 1st hole transport layer with a film thickness of 80 nm was formed. Next, the compound HT-2 was vapor-deposited on this 1st hole transport layer, and the 2nd hole transport layer with a film thickness of 10 nm was formed.

After forming the hole injection layer and the hole transport layer in this way, H1 as a host material, compound A-1-1 as a TADF light emitting material, and D1 as a dopant material were co-deposited thereon to form a light emitting layer with a thickness of 25 nm. The concentration of the compound A-1-1 in the light emitting layer was 50 mass%, the concentration of the host (H1) was 49 mass%, and the concentration of the dopant (D1) was 1 mass%.

Next, the compound HB was vapor-deposited on this light emitting layer, and the 5 nm-thick hole blocking layer was formed. Then, on this barrier layer, compound ET was vapor-deposited to form an electron transport layer with a film thickness of 20 nm.

Next, lithium fluoride (LiF) was vapor-deposited on this electron transport layer, and the electron injection layer with a film thickness of 1 nm was formed. Then, on the electron injection layer, metallic aluminum (Al) was vapor-deposited to form a metallic Al cathode having a thickness of 80 nm, thereby producing an organic light emitting device.

Examples 2 to 36)

The organic light emitting devices of Examples 2 to 36 were prepared in the same manner as in Example 1 except that the compound shown in Table 6 was used instead of the compound A-1-1 of the light emitting layer of Example 1.

Comparative Example 1)

The organic light emitting device of Comparative Example 1 was manufactured in the same manner as in Example 1 except that Comparative Compound 1 was used instead of Compound A-1-1 of the light emitting layer of Example 1.

Comparative Example 2)

The organic light emitting device of Comparative Example 2 was manufactured in the same manner as in Example 1 except that Comparative Compound 2 was used instead of Compound A-1-1 of the light emitting layer of Example 1.

Comparative Example 3)

The organic light emitting device of Comparative Example 3 was manufactured in the same manner as in Example 1 except that Comparative Compound 3 was used instead of Compound A-1-1 of the light emitting layer of Example 1.

For the organic light emitting devices manufactured according to Examples 1 to 36 and Comparative Examples 1 to 3, voltage, luminous efficiency, and color coordinates were measured, and the results are shown in Table 6 below.

compound drive voltage
(V) Luminous Efficiency
(cd/A) color coordinates x y Example 1 A-1-1 3.51 51.7 0.347 0.621 Example 2 A-1-2 3.62 51.2 0.341 0.618 Example 3 A-1-8 3.41 47.1 0.382 0.561 Example 4 A-2-14 3.66 43.4 0.348 0.619 Example 5 A-2-17 3.74 48.5 0.341 0.579 Example 6 A-2-29 3.75 47.4 0.346 0.597 Example 7 A-3-1 3.80 50.7 0.381 0.581 Example 8 A-3-2 3.78 50.3 0.321 0.628 Example 9 A-3-8 3.64 51.7 0.374 0.621 Example 10 A-4-14 3.53 51.2 0.376 0.630 Example 11 A-4-17 3.44 51.3 0.364 0.621 Example 12 A-4-29 3.74 51.6 0.326 0.630 Example 13 A-5-1 3.55 50.1 0.342 0.610 Example 14 A-5-2 3.75 50.2 0.335 0.613 Example 15 A-5-8 3.51 51.3 0.351 0.583 Example 16 A-6-14 3.49 52.6 0.363 0.591 Example 17 A-6-17 3.74 50.7 0.366 0.596 Example 18 A-6-29 3.68 51.1 0.349 0.562 Example 19 B-1-1 3.69 46.4 0.344 0.611 Example 20 B-1-2 3.78 43.5 0.346 0.607 Example 21 B-1-8 3.83 46.7 0.339 0.612 Example 22 B-2-14 3.59 51.3 0.371 0.603 Example 23 B-2-17 3.67 49.2 0.375 0.592 Example 24 B-2-29 3.76 48.4 0.346 0.601 Example 25 B-3-1 3.65 47.1 0.354 0.621 Example 26 B-3-2 3.73 46.6 0.366 0.632 Example 27 B-3-8 3.87 45.0 0.371 0.603 Example 28 B-4-14 3.61 46.8 0.354 0.612 Example 29 B-4-17 3.77 49.2 0.356 0.616 Example 30 B-4-29 3.86 48.5 0.369 0.610 Example 31 B-5-1 3.73 47.8 0.356 0.606 Example 32 B-5-2 3.74 46.0 0.341 0.611 Example 33 B-5-8 3.67 47.5 0.375 0.612 Example 34 B-6-14 3.57 48.6 0.374 0.633 Example 35 B-6-17 3.68 47.5 0.352 0.615 Example 36 B-6-29 3.70 47.7 0.361 0.624 Comparative Example 1 Comparative compound 1 4.74 40.1 0.173 0.237 Comparative Example 2 Comparative compound 2 4.91 37.5 0.301 0.472 Comparative Example 3 Comparative compound 3 4.43 34.5 0.232 0.542

As can be seen from the results in Table 6, Examples 1 to 36 using the compound according to the present invention exhibit a much lower driving voltage and high luminous efficiency and color coordinates suitable for green than Comparative Examples 1 to 3 using the comparative compound. Confirmed.

100: substrate
200: positive electrode
300: organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (11)

A heterocyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ to X ₃ are each independently N or CR _A , and at least two are N,
R _A and R ₁ are hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
D _A and D _B are each independently represented by the following formula (2),
[Formula 2]

In Formula 2,
Y is a direct bond; O; S; NR _B ; or CR _C R _D ,
R ₁₁ to R ₁₈ , and R _B to R _D are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Groups of adjacent R ₁₁ to R _18, and R _B to R _D may form a substituted or unsubstituted ring by combining to each other,

is a position bonded to Formula 1 above. The method according to claim 1,
Formula 1 is a heterocyclic compound represented by the following Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, the definition of each substituent is the same as the definition in Formula 1. The method according to claim 1,
Formula 2 is a heterocyclic compound represented by any one of the following Formulas 2-1 to 2-6:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,
Y ₁ is O; S; NR _E ; or CR _F R _G ,
Z is O; S; NR _H ; or CR _I R _J ,
R _E to R _J and R ₂₁ to R ₂₄ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r21 and r24 are each an integer from 1 to 8,
r22 and r23 are each an integer from 1 to 10,
When each of r21 to r24 is 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
Wherein R ₁ is a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted pyridine group is a heterocyclic compound. The method according to claim 1,
The D _A and D _B are the same as each other heterocyclic compound. The method according to claim 1,
ΔE _ST (S ₁ -T ₁ ) of the heterocyclic compound is a heterocyclic compound that is 0.3 or less. The method according to claim 1,
The formula 1 is a heterocyclic compound represented by any one of the following compounds:

. a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode,
The organic material layer is an organic light emitting device comprising at least one heterocyclic compound according to any one of claims 1 to 7. 9. The method of claim 8,
The organic material layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound. 10. The method of claim 9,
The light emitting layer may further include a host material and a dopant material. 9. The method of claim 8,
The organic light emitting device further comprises one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

Images