KR20220000215A - Heterocyclic compound and organic light emitting device comprising 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 compound can be used as a material for a light emitting layer of the organic light emitting device. For example, the compound can be used alone as a light emitting material, or can be used as a host material of the light emitting layer.

Description

Heterocyclic compound and organic light emitting device comprising the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

The organic electroluminescent device is a kind of self-emission type 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 an organic light emitting diode, the development of a material for an organic thin film is continuously required.

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

A compound having a chemical structure that can satisfy conditions required for materials usable in an organic light-emitting device, such as an appropriate energy level, electrochemical stability, and thermal stability, and can play various roles required in an organic light-emitting device according to a substituent Research on organic light emitting devices including

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

[Formula 1]

In Formula 1,

X is O; or S;

N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,

L and L1 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group, a and d are integers of 1 to 4,

Y is O; S; CR _x R _y ; or NR _z ,

R ₁ to R ₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle, and b is an integer of 1 to 4 and c is an integer from 1 to 3,

The b + c ≤ 6,

The R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

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

The compound described herein can be used as an organic material layer of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. in the organic light emitting device. In particular, the compound can be used as a material for a light emitting layer of an organic light emitting device. For example, the compound may be used alone as a light emitting material or may be used as a host material of the light emitting layer.

In particular, the compound of Formula 1 according to the present application has a more electronically stable structure by substituting an N-containing ring and a condensed carbazole structure on the benzene ring of the dibenzofuran/dibenzothiophene structure, thereby improving the device lifespan. can

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

Hereinafter, the present application will be described in detail.

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 not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

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 alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.

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 means a group in which a cycloalkyl group is directly connected to another ring group or condensed. 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 ring 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 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 S, O, 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, 5,11-dihydroindeno [1,2-b ] a carbazolyl group, and the like, but is not limited thereto.

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, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. In addition, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

In the present specification, the phosphine oxide group may be specifically substituted with an aryl group, and the above-described examples of the aryl group may be applied. For example, the phosphine oxide group includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.

As used herein, "adjacent" group means 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 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 heterocycle that adjacent groups may form is not a monovalent group.

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

In an exemplary embodiment of the present application, X may be O.

In an exemplary embodiment of the present application, X may be S.

는 결합 위치 또는 치환 위치를 의미할 수 있다.In this application,

may mean a bonding position or a substitution position.

In the exemplary embodiment of the present application, Chemical Formula 1 may be represented by Chemical Formula 2 or 3 below.

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

Each substituent is the same as defined in Formula 1,

1A to 1D and 1A' to 1D' refer to the bonding positions of the substituents, respectively,

는 1A, 1C 및 1D 중 어느 하나와 결합한다.In Formula 2, when -(L)aN-Het is bonded to 1A', the

binds to any one of 1A, 1C and 1D.

는 1A에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 2 is bonded to 1A', the

can bind to 1A.

는 1C에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 2 is bonded to 1A', the

can bind to 1C.

는 1D에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 2 is bonded to 1A', the

can bind to 1D.

는 1A 내지 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when the -(L)aN-Het of Formula 2 is bonded to 1B', the

may bind to any one of 1A to 1D.

는 1A 내지 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when the -(L)aN-Het of Formula 2 is bonded to 1 C', the

may bind to any one of 1A to 1D.

는 1A 내지 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 2 is bonded to 1 D', the

may bind to any one of 1A to 1D.

는 1B 내지 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when the -(L)aN-Het of Formula 3 binds to 1 A, the

may bind to any one of 1B to 1D.

는 1A, 1C 및 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when the -(L)aN-Het of Formula 3 binds to 1 B, the

may bind to any one of 1A, 1C and 1D.

는 1A, 1B 및 1D 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 3 is bonded to 1 C, the

may bind to any one of 1A, 1B and 1D.

는 1A 내지 1C 중 어느 하나에 결합할 수 있다.In the exemplary embodiment of the present application, when -(L)aN-Het of Formula 3 is bonded to 1 D, the

may bind to any one of 1A to 1C.

In the exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 4 to 8 below.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 4 to 8,

The definition of each substituent is the same as the definition in Formula 1 above.

는 하기 화학식 1-1 또는 1-2로 표시될 수 있다.In an exemplary embodiment of the present application, the 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 above.

는 하기 화학식 2-1 내지 2-5 중 어느 하나로 표시될 수 있다.In an exemplary embodiment of the present application, the formula (1)

may be represented by any one of the following Chemical Formulas 2-1 to 2-5.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,

The definitions of Y, L1 and d are the same as the definitions in Formula 1 above,

Ar is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present application, N-Het is a monocyclic or polycyclic heterocycle including one or more N-substituted or unsubstituted.

In another exemplary embodiment, N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C60 aryl group and a C2 to C60 heteroaryl group, and N is one or more and three or less. It is a monocyclic or polycyclic heterocycle containing.

In another exemplary embodiment, N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group, and N is one or more It is a monocyclic or polycyclic heterocycle containing 3 or less.

In another exemplary embodiment, N-Het is a substituted or unsubstituted triazine group; pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted benzo[4,5]thieno[3,2-d]pyrimidine group; Or it may be a substituted or unsubstituted benzofuro[3,2-d]pyrimidine group.

In another exemplary embodiment, N-Het is a triazine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a pyrimidine group unsubstituted or substituted with a phenyl group; a quinazoline group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a benzo[4,5]thieno[3,2-d]pyrimidine group substituted or unsubstituted with a phenyl group; Alternatively, it may be a benzofuro[3,2-d]pyrimidine group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present application, L and L1 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L and L1 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another exemplary embodiment, L and L1 are the same as or different from each other, and each independently a direct bond; C6 to C40 arylene group; Or it may be a C2 to C40 heteroarylene group.

In another exemplary embodiment, L and L1 may be a direct bond.

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

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

In an exemplary embodiment of the present application, Y may be CRaRb.

In the exemplary embodiment of the present application, Y may be NRc.

In an exemplary embodiment of the present application, R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other may combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.

In another exemplary embodiment, R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other may combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.

In another exemplary embodiment, R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen; C6 to C40 aryl group; Or it may be a C2 to C40 heteroaryl group.

In another exemplary embodiment, R ₉ and R ₁₀ are It may be hydrogen.

In an exemplary embodiment of the present application, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other may combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; and a substituted or unsubstituted C6 to C60 aryl group, or two or more groups adjacent to each other may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; And two or more groups selected from the group consisting of a C6 to C60 aryl group or adjacent to each other may combine with each other to form a C6 to C60 aromatic hydrocarbon ring.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; And two or more groups selected from the group consisting of a C6 to C40 aryl group or adjacent to each other may combine with each other to form a C6 to C40 aromatic hydrocarbon ring.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; and C6 to C40 monocyclic or polycyclic aryl groups, or two or more groups adjacent to each other may combine with each other to form a C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring.

In another exemplary embodiment, R _{1 To} R _{8 Are} the same as or different from each other, and each independently hydrogen; And two or more groups selected from the group consisting of or adjacent to each other may combine with each other to form a benzene ring.

In an exemplary embodiment of the present application, R ₁ to R ₈ may be hydrogen.

In the exemplary embodiment of the present application, _{at least one of R 1} to R ₄ may be a substituted or unsubstituted C6 to C60 aryl group, and R ₅ to R ₈ may be hydrogen.

In an exemplary embodiment of the present application, _{at least one of R 5} to R ₈ may be a substituted or unsubstituted C6 to C60 aryl group, and R ₁ to R ₄ may be hydrogen.

In an exemplary embodiment of the present application, _{two groups adjacent to each other among R 1} to R ₄ are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and R ₁ to R ₄ are the remaining unbonded groups. A substituent and R ₅ to R ₈ may be hydrogen.

In the exemplary embodiment of the present application, _{two groups adjacent to each other among R 5} to R ₈ are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and the _{remainder of R 5} to R ₈ that is not bonded A substituent and R ₁ to R ₄ may be hydrogen.

In an exemplary embodiment of the present application, Ar is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ar is a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ar may be a substituted or unsubstituted C6 to C20 aryl group.

In another exemplary embodiment, Ar may be a C6 to C20 aryl group.

In another exemplary embodiment, Ar may be a phenyl group.

In an exemplary embodiment of the present application, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; Or it may be a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; Or it may be a substituted or unsubstituted C6 to C40 aryl group.

In another embodiment, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; Or it may be a C6 to C40 aryl group.

In another embodiment, the R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; or a phenyl group.

According to an exemplary embodiment of the present application, 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 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.

On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

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

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

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

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the blue organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the green organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the red organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the light emitting layer of the green organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the light emitting layer of the red organic light emitting device.

Specific details of the heterocyclic compound represented by Formula 1 are the same as described above.

The organic light emitting device of the present invention 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 heterocyclic compound.

The heterocyclic 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 invention 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.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

In the organic light emitting device according to an exemplary embodiment of the present application, the organic material layer including the heterocyclic compound represented by Formula 1 provides an organic light emitting device that further includes a heterocyclic compound represented by the following Formula A .

[Formula A]

In the formula A,

Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR ₁₁ R ₁₂ R ₁₃ ; -P(=O)R ₁₁ R ₁₂ ; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring, ,

R _{11 ,} R _{12 ,} and R ₁₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r and s are integers from 0 to 7.

When the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A are included in the organic material layer of the organic light emitting device, better efficiency and lifespan effects are exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, and thus the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan.

In an exemplary embodiment of the present application, Formula A may be represented by Formula A-1 or Formula A-2 below.

[Formula A-1]

[Formula A-2]

In Formulas A-1 and A-2,

The definitions of Rc, Rd, r and s are the same as in the above formula (A),

Ra1, Rb1 and Rc1 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group,

R1' and R2' are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group,

L1' is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,

Ar1' is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted, C2 to C60 heteroaryl group comprising at least one of S and O,

m' is an integer from 0 to 4,

n' is an integer from 0 to 2.

In the exemplary embodiment of the present application, Rc and Rd of Formula A may be hydrogen.

In the exemplary embodiment of the present application, Ra1 and Rb1 of Formula A-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Ra1 and Rb1 of Formula A-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ra1 and Rb1 of Formula A-1 are the same as or different from each other, and each independently a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN and -SiR ₁₀₁ R ₁₀₂ R ₁₀₃ It may be a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of

In another exemplary embodiment, Ra1 and Rb1 of Formula A-1 are the same as or different from each other, and each independently a phenyl group, a phenyl group unsubstituted or substituted with _{-CN or -SiR 101} R ₁₀₂ R _{103 ;} a biphenyl group unsubstituted or substituted with a phenyl group; naphthyl group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; spirobifluorene group; Or it may be a triphenylene group.

In the exemplary embodiment of the present application, R _{101 ,} R _{102 ,} and R ₁₀₃ of Formula A-1 may be the same as or different from each other and each independently a substituted or unsubstituted C6 to C60 aryl group.

In the exemplary embodiment of the present application, R _{101 ,} R _{102 ,} and R ₁₀₃ of Formula A-1 may be the same as or different from each other and each independently a substituted or unsubstituted C6 to C40 aryl group.

In the exemplary embodiment of the present application, R _{101 ,} R _{102 ,} and R ₁₀₃ of Formula A-1 may be the same as or different from each other and each independently a C6 to C60 aryl group.

In the exemplary embodiment of the present application, R _{101 ,} R _{102 ,} and R ₁₀₃ of Formula A-1 may be a phenyl group.

In the exemplary embodiment of the present application, Rc1 of Formula A-2 may be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Rc1 in Formula A-2 may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Rc1 in Formula A-2 may be a C6 to C40 aryl group.

In another exemplary embodiment, Rc1 in Formula A-2 may be a phenyl group.

In an exemplary embodiment of the present application, R1' and R2' of Formula A-2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R1′ and R2′ of Formula A-2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, R1′ and R2′ of Formula A-2 are the same as or different from each other, and each independently hydrogen; C1 to C40 alkyl group; C6 to C40 aryl group; Or it may be selected from the group consisting of a C2 to C40 heteroaryl group.

In another exemplary embodiment, R1′ and R2′ in Formula A-2 may be hydrogen.

In an exemplary embodiment of the present application, L1' of Formula A-2 is a direct bond; Or it may be a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L1' of Formula A-2 is a direct bond; Or it may be a substituted or unsubstituted C6 to C40 arylene group.

In another exemplary embodiment, L1' of Formula A-2 is a direct bond; Or it may be a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L1' of Formula A-2 is a direct bond; Or it may be a C6 to C20 arylene group.

In another exemplary embodiment, L1' of Formula A-2 is a direct bond; or a phenylene group.

In an exemplary embodiment of the present application, Ar1' of Formula A-2 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group including at least one of S and O.

In another exemplary embodiment, Ar1' of Formula A-2 is a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted, C2 to C40 heteroaryl group including at least one of S and O.

In another exemplary embodiment, Ar1′ in Formula A-2 is a C6 to C40 aryl group unsubstituted or substituted with a C1 to C10 alkyl group; Or it may be a substituted or unsubstituted, C2 to C40 heteroaryl group including at least one of S and O.

In another exemplary embodiment, Ar1' of Formula A-2 is a phenyl group; biphenyl group; naphthyl group; dimethyl fluorenyl group; dibenzothiophene group; Or it may be a dibenzofuran group.

In addition, another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1, and the heterocyclic compound represented by Formula A.

Specific details of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A are the same as described above.

The weight ratio of the heterocyclic compound represented by Formula 1 in the composition to the heterocyclic compound represented by Formula A may be 1: 10 to 10: 1, 1: 8 to 8: 1, and 1: 5 to 5: 1 may be, and may be 1: 2 to 2: 1, but is not limited thereto.

The composition may be used when forming an organic material of an organic light emitting device, and in particular, it may be more preferably used when forming a host of a light emitting layer.

In an exemplary embodiment of the present application, the organic material layer includes a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula A, and may be used together with a phosphorescent dopant.

In the exemplary embodiment of the present application, the organic material layer includes the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A, and may be used together with an iridium-based dopant.

As the phosphorescent dopant material, those known in the art may be used.

For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L ₂ MX' and L ₃ M may be used, but the scope of the present invention is not limited by these examples. .

Here, L, L', L", X' and X" are different bidentate ligands, and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, or the like.

L is an anionic bidentate ligand coordinated to M with the iridium-based dopant by sp2 carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -benzoquinoline), (thiophenepyrizine), phenylpyridine, benzothiophenepyrizine, 3-methoxy-2-phenylpyridine, thiophenepyrizine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

In the exemplary embodiment of the present application, as the iridium-based dopant, (piq) ₂ (Ir)(acac) may be used as the red phosphorescent dopant.

In the exemplary embodiment of the present application, the content of the dopant may be 1 to 15 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the total composition included in the light emitting layer.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron transport layer, a light emitting layer, or a hole blocking layer, and the electron transport layer, the light emitting layer or the hole blocking layer may include the heterocyclic compound.

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

In an exemplary embodiment of the present application, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application. A method of manufacturing an organic light emitting device is provided.

In an exemplary embodiment of the present application, the step of forming the organic material layer is to pre-mix the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A to form using a thermal vacuum deposition method. Provided is a method for manufacturing a phosphorus organic light emitting diode.

The pre-mixed refers to mixing the materials in one park before depositing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A on the organic layer.

The premixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.

The organic material layer including Formula 1 may further include other materials as needed.

The organic material layer including Formula 1 and Formula A at the same time may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the compound of Formula 1 or Formula A 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); ZnO: Al or SnO ₂ : Combination of metals and oxides such as 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 anode material, and a 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 US Pat. No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type 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), polyaniline/Dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) and the like may 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 individual sources, or may be premixed and deposited as a single source for use. 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 alone, but materials in which the host material and the dopant material together participate in light emission may be used.

When mixing and using a host of a 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 and 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 application may be a top emission type, a back emission type, or a double side emission type depending on a material used.

The heterocyclic compound according to an exemplary embodiment of the present application 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 ] Preparation of compound D

1) Preparation of Intermediate C

Intermediate A (10 g, 50.75 mmol), Intermediate B (9.3 g, 55.83 mmol), Pd(PPh ₃ ) ₄ (5.9 g, 5.08 mmol) and K ₂ CO ₃ (14 g, 101.5 mmol) were mixed with 1,4-dioxane (1,4-Dioxane) (100 mL) and distilled water (20 mL) were dissolved and stirred at 120° C. for 4 hours. The reaction mixture was dissolved in methylene chloride (Methylene Chloride, MC), extracted with water, and the organic layer was dried over anhydrous MgSO ₄ and filtered through silica gel. The solvent was removed from the filtered filtrate by a rotary evaporator to obtain 10.7 g of intermediate C as a yellow oil in 88% yield.

2) Preparation of compound D

Intermediate C (10.7 g, 44.73 mmol) and PPh ₃ (29.33 g, 111.82 mmol) was dissolved in 1,2-DCB and stirred overnight at 130 °C. The reaction mixture was dissolved in methylene chloride (Methylene Chloride, MC), extracted with water, and the organic layer was dried over anhydrous MgSO ₄ and filtered through silica gel. The solvent was removed from the filtered filtrate by a rotary evaporator to obtain 6.7 g of Intermediate D as a white solid in 73% yield.

In Preparation Example 1, the compounds used in Intermediate A and Intermediate B were prepared in the same manner as in Preparation Example 1, except that the compounds of Table 1 below were used, to prepare Intermediate D, respectively.

[ production example 2] Preparation of compound 1

1) Preparation of Intermediate G

Intermediate F (10g, 35.52mmol), Bis(pinacolato)diboron) (13.5g, 53.28mmol), PdCl ₂ dppf ([1,1'-bis(diphenylphosphino)ferrocene ] Dichloropalladium (IF) (1.3 g, 1.78 mmol) and KOAc (potassium acetate) (8.7 g, 88.80 mmol) were dissolved in 1,4-dioxane (100 mL), followed by stirring at 100° C. for 2 hours. After concentration, the mixture was dissolved with MC, extracted with water, and the organic layer was dried over anhydrous MgSO ₄ and filtered through silica gel. The filtered filtrate was removed with a rotary evaporator to remove the solvent, and intermediate G, a brown solid, was obtained in a crude state without further purification.

2) Preparation of Intermediate I

Intermediate G (8 g, 24.34 mmol), Intermediate H (2-chloro-4,6-diphenyl-1,3,5-triazine) ) (6.5 g, 24.34 mol), Pd(PPh ₃ ) ₄ (Tetrakis(triphenylphosphine)palladium(0)) (1.4 g, 1.22 mmol) and K ₂ CO ₃ (6.7 g, 48.68 mmol) in dioxane (80 mL) and H ₂ O (16 mL) and stirred at 100° C. for 2 hours. After completion of the reaction, the precipitated solid was filtered and washed with H ₂ O, methanol and acetone to obtain 9.1 g of Intermediate I as a white solid in 86% yield.

3) Preparation of compound 1

Intermediate I (6.5 g, 14.98 mmol), Intermediate D (3.1 g, 13.83 mmol), Pd ₂ (dba) ₃ (Tris(dibenzylideneacetone)dipalladium(0)) (0.68 g, 0.75 mmol), XPhos (0.71 g, 1.50) mmol) and Na ^t Obu (Sodium tert-butoxide) (2.9 g, 29.96 mmol) were dissolved in toluene (65 mL) and stirred at 100° C. for 3 hours. After completion of the reaction, the precipitated solid was filtered and washed with H ₂ O and acetone. After drying the filtered solid, it was dissolved in an excess of hot 1,2-dichlorobenzene (1,2-Dichlorobenzene) solvent and filtered through silica gel. After removing the solvent from the filtered filtrate with a rotary evaporator, precipitation with acetone, and filtering the precipitate, 6.6 g of Compound 1 as a white solid was obtained in 73% yield.

The target compound shown in Table 2 was synthesized in the same manner as in Preparation Example 2, except that Intermediates F, H and D of Table 2 were used instead of Intermediates F, H and D of Preparation Example 2.

In addition to the compounds shown in Table 2, compounds usable as Intermediate H are as follows.

Compounds other than the compounds described in Preparation Examples 1 and 2 were prepared in the same manner as the compounds described in Preparation Examples 1 and 2, and the synthesis confirmation results are shown in Tables 3 and 4 below.

compound FD-Mass compound FD-Mass One m/z=604.65 (C41H24N4O2=604.19) 2 m/z=654.71 (C45H26N4O2=654.21) 3 m/z=654.71 (C45H26N4O2=654.21) 4 m/z=654.71 (C45H26N4O2=654.21) 5 m/z=654.71 (C45H26N4O2=654.21) 6 m/z=654.71 (C45H26N4O2=654.21) 7 m/z=654.71 (C45H26N4O2=654.21) 8 m/z=680.75 (C47H28N4O2=680.22) 9 m/z=680.75 (C47H28N4O2=680.22) 10 m/z=620.72 (C41H24N4OS=620.17) 11 m/z=670.78 (C45H26N4O = 670.18) 12 m/z=670.78 (C45H26N4OS=670.18) 13 m/z=670.78 (C45H26N4OS= 670.18) 14 m/z=670.78 (C45H26N4OS=670.18) 15 m/z=670.78 (C45H26N4OS= 670.18) 16 m/z=670.78 (C45H26N4OS=670.18) 17 m/z=696.82 (C47H28N4OS=696.20) 18 m/z=696.82 (C47H28N4OS=696.20) 19 m/z = 679.77 (C47H29N5O = 679.24) 20 m/z= 729.82 (C51H31N5O=729.25) 21 m/z= 729.82 (C51H31N5O=729.25) 22 m/z= 729.82 (C51H31N5O=729.25) 23 m/z= 729.82 (C51H31N5O=729.25) 24 m/z= 729.82 (C51H31N5O=729.25) 25 m/z= 729.82 (C51H31N5O=729.25) 26 m/z = 755.86 (C53H33N5O=755.27) 27 m/z = 755.86 (C53H33N5O=755.27) 28 m/z=746.88 (C51H30N4OS=746.21) 29 m/z=696.82 (C47H28N4OS=696.20) 30 m/z=746.88 (C51H30N4OS=746.21) 31 m/z=746.88 (C51H30N4OS=746.21) 32 m/z=746.88 (C51H30N4OS=746.21) 33 m/z=746.88 (C51H30N4OS=746.21) 34 m/z=746.88 (C51H30N4OS=746.21) 35 m/z=772.91 (C53H32N4OS=772.23) 36 m/z=772.91 (C53H32N4OS=772.23) 37 m/z = 712.88 (C47H28N4S2 = 712.18) 38 m/z=762.94 (C51H30N4S2=762.19) 39 m/z = 762.94 (C51H30N4S2 = 762.19) 40 m/z=762.94 (C51H30N4S2=762.19) 41 m/z=762.94 (C51H30N4S2=762.19) 42 m/z=762.94 (C51H30N4S2=762.19) 43 m/z=762.94 (C51H30N4S2=762.19) 44 m/z=88.98 (C53H32N4S2=788.21) 45 m/z=88.98 (C53H32N4S2=788.21) 46 m/z= 695.83 (C47H29N5S= 695.21) 47 m/z= 745.89 (C51H31N5S= 745.23) 48 m/z= 745.89 (C51H31N5S= 745.23) 49 m/z= 745.89 (C51H31N5S= 745.23) 50 m/z= 745.89 (C51H31N5S= 745.23) 51 m/z= 745.89 (C51H31N5S= 745.23) 52 m/z= 745.89 (C51H31N5S= 745.23) 53 m/z= 771.93 (C53H33N5S= 771.25) 54 m/z= 771.93 (C53H33N5S= 771.25) 55 m/z=604.65 (C41H24N4O2=604.19) 56 m/z=654.71 (C45H26N4O2=654.21) 57 m/z=654.71 (C45H26N4O2=654.21) 58 m/z=654.71 (C45H26N4O2=654.21) 59 m/z=654.71 (C45H26N4O2=654.21) 60 m/z=654.71 (C45H26N4O2=654.21) 61 m/z=654.71 (C45H26N4O2=654.21) 62 m/z=680.75 (C47H28N4O2=680.22) 63 m/z=680.75 (C47H28N4O2=680.22) 64 m/z=696.82 (C47H28N4OS=696.20) 65 m/z=746.88 (C51H30N4OS=746.21) 66 m/z=746.88 (C51H30N4OS=746.21) 67 m/z=746.88 (C51H30N4OS=746.21) 68 m/z=746.88 (C51H30N4OS=746.21) 69 m/z=746.88 (C51H30N4OS=746.21) 70 m/z=746.88 (C51H30N4OS=746.21) 71 m/z=772.91 (C53H32N4OS= 772.23) 72 m/z=772.91 (C53H32N4OS=772.23) 73 m/z = 679.77 (C47H29N5O = 679.24) 74 m/z = 729.82 (C51H31N5O = 729.25) 75 m/z = 729.82 (C51H31N5O = 729.25) 76 m/z = 729.82 (C51H31N5O = 729.25) 77 m/z = 729.82 (C51H31N5O = 729.25) 78 m/z = 729.82 (C51H31N5O = 729.25) 79 m/z = 729.82 (C51H31N5O = 729.25) 80 m/z = 755.86 (C53H33N5O=755.27) 81 m/z = 755.86 (C53H33N5O=755.27) 82 m/z=604.65 (C41H24N4O2=604.19) 83 m/z=654.71 (C45H26N4O2=654.21) 84 m/z=654.71 (C45H26N4O2=654.21 85 m/z=654.71 (C45H26N4O2=654.21 86 m/z=654.71 (C45H26N4O2=654.21 87 m/z=654.71 (C45H26N4O2=654.21 88 m/z=654.71 (C45H26N4O2=654.21 89 m/z=680.75 (C47H28N4O2=680.22) 90 m/z=680.75 (C47H28N4O2=680.22) 91 m/z=620.72 (C41H24N4OS= 620.17) 92 m/z=670.78 (C45H26N4OS=670.18) 93 m/z=670.78 (C45H26N4OS=670.18) 94 m/z=670.78 (C45H26N4OS=670.18) 95 m/z=670.78 (C45H26N4OS=670.18) 96 m/z=670.78 (C45H26N4OS=670.18) 97 m/z=670.78 (C45H26N4OS=670.18) 98 m/z=696.82 (C47H28N4OS=696.20) 99 m/z=696.82 (C47H28N4OS=696.20) 100 m/z = 679.77 (C47H29N5O = 679.24) 101 m/z= 729.82 (C51H31N5O=729.25) 102 m/z= 729.82 (C51H31N5O=729.25) 103 m/z= 729.82 (C51H31N5O=729.25) 104 m/z= 729.82 (C51H31N5O=729.25) 105 m/z= 729.82 (C51H31N5O=729.25) 106 m/z= 729.82 (C51H31N5O=729.25) 107 m/z= 755.86 (C53H33N5O=755.27) 108 m/z= 755.86 (C53H33N5O=755.27) 109 m/z = 604.65 (C41H24N4O2 = 604.19) 110 m/z=654.71 (C45H26N4O2=654.21) 111 m/z=654.71 (C45H26N4O2=654.21) 112 m/z=654.71 (C45H26N4O2=654.21) 113 m/z=654.71 (C45H26N4O2=654.21) 114 m/z=654.71 (C45H26N4O2=654.21) 115 m/z=654.71 (C45H26N4O2=654.21) 116 m/z=680.75 (C47H28N4O2=680.22) 117 m/z=680.75 (C47H28N4O2=680.22) 118 m/z=620.72 (C41H24N4OS=620.17) 119 m/z=670.78 (C45H26N4OS= 670.18) 120 m/z=670.78 (C45H26N4OS=670.18) 121 m/z=670.78 (C45H26N4OS= 670.18) 122 m/z=670.78 (C45H26N4OS=670.18) 123 m/z=670.78 (C45H26N4OS= 670.18) 124 m/z=670.78 (C45H26N4OS=670.18) 125 m/z=696.82 (C47H28N4OS=696.20) 126 m/z=696.82 (C47H28N4OS=696.20) 127 m/z= 729.82 (C51H31N5O=729.25) 128 m/z= 779.88 (C55H33N5O=779.27) 129 m/z= 779.88 (C55H33N5O=779.27) 130 m/z= 779.88 (C55H33N5O=779.27) 131 m/z= 779.88 (C55H33N5O=779.27) 132 m/z= 779.88 (C55H33N5O=779.27) 133 m/z= 779.88 (C55H33N5O=779.27) 134 m/z = 805.92 (C57H35N5O=805.28) 135 m/z = 805.92 (C57H35N5O=805.28) 136 m/z = 604.65 (C41H24N4O2 = 604.19) 137 m/z=654.71 (C45H26N4O2=654.21) 138 m/z=654.71 (C45H26N4O2=654.21) 139 m/z=654.71 (C45H26N4O2=654.21) 140 m/z=654.71 (C45H26N4O2=654.21) 141 m/z=654.71 (C45H26N4O2=654.21) 142 m/z=654.71 (C45H26N4O2=654.21) 143 m/z=680.75 (C47H28N4O2=680.22) 144 m/z=680.75 (C47H28N4O2=680.22) 145 m/z=620.72 (C41H24N4OS= 620.17) 146 m/z=670.78 (C45H26N4OS=670.18) 147 m/z=670.78 (C45H26N4OS=670.18) 148 m/z=670.78 (C45H26N4OS=670.18) 149 m/z=670.78 (C45H26N4OS=670.18) 150 m/z=670.78 (C45H26N4OS=670.18) 151 m/z=670.78 (C45H26N4OS=670.18) 152 m/z=696.82 (C47H28N4OS=696.20) 153 m/z=696.82 (C47H28N4OS=696.20) 154 m/z = 679.77 (C47H29N5O = 679.24) 155 m/z= 729.82 (C51H31N5O=729.25) 156 m/z= 729.82 (C51H31N5O=729.25) 157 m/z= 729.82 (C51H31N5O=729.25) 158 m/z= 729.82 (C51H31N5O=729.25) 159 m/z= 729.82 (C51H31N5O=729.25) 160 m/z= 729.82 (C51H31N5O=729.25) 161 m/z=755.86 (C53H33N5O=755.27) 162 m/z=755.86 (C53H33N5O=755.27) 163 m/z = 604.65 (C41H24N4O2 = 604.19) 164 m/z=654.71 (C45H26N4O2=654.21) 165 m/z=654.71 (C45H26N4O2=654.21) 166 m/z=654.71 (C45H26N4O2=654.21) 167 m/z=654.71 (C45H26N4O2=654.21) 168 m/z=654.71 (C45H26N4O2=654.21) 169 m/z=654.71 (C45H26N4O2=654.21) 170 m/z=680.75 (C47H28N4O2=680.22) 171 m/z=680.75 (C47H28N4O2=680.22) 172 m/z=620.72 (C41H24N4OS=620.17) 173 m/z=670.78 (C45H26N4OS= 670.18) 174 m/z=670.78 (C45H26N4OS=670.18) 175 m/z=670.78 (C45H26N4OS= 670.18) 176 m/z=670.78 (C45H26N4OS=670.18) 177 m/z=670.78 (C45H26N4OS= 670.18) 178 m/z=670.78 (C45H26N4OS=670.18) 179 m/z=696.82 (C47H28N4OS=696.20) 180 m/z=696.82 (C47H28N4OS=696.20) 181 m/z = 679.77 (C47H29N5O=679.24) 182 m/z=729.82 (C51H31N5O=729.25) 183 m/z=729.82 (C51H31N5O=729.25) 184 m/z=729.82 (C51H31N5O=729.25) 185 m/z=729.82 (C51H31N5O=729.25) 186 m/z=729.82 (C51H31N5O=729.25) 187 m/z=729.82 (C51H31N5O=729.25) 188 m/z= 755.86 (C53H33N5O=755.27) 189 m/z= 755.86 (C53H33N5O=755.27) 190 m/z=654.71 (C45H26N4O2=654.21) 191 m/z=704.77 (C49H28N4O2=704.22) 192 m/z=704.77 (C49H28N4O2=704.22) 193 m/z=704.77 (C49H28N4O2=704.22) 194 m/z=704.77 (C49H28N4O2=704.22) 195 m/z=704.77 (C49H28N4O2=704.22) 196 m/z=704.77 (C49H28N4O2=704.22) 197 m/z=730.81 (C51H30N4O2=730.24) 198 m/z=730.81 (C51H30N4O2=730.24) 199 m/z=620.72 (C41H24N4OS= 620.17) 200 m/z=670.78 (C45H26N4OS=670.18) 201 m/z=670.78 (C45H26N4OS=670.18) 202 m/z=670.78 (C45H26N4OS=670.18) 203 m/z=670.78 (C45H26N4OS=670.18) 204 m/z=670.78 (C45H26N4OS=670.18) 205 m/z=670.78 (C45H26N4OS=670.18) 206 m/z=696.82 (C47H28N4OS=696.20) 207 m/z=696.82 (C47H28N4OS=696.20) 208 m/z= 729.82 (C51H31N5O=729.25) 209 m/z= 779.88 (C55H33N5O=779.27) 210 m/z= 779.88 (C55H33N5O=779.27) 211 m/z= 779.88 (C55H33N5O=779.27) 212 m/z= 779.88 (C55H33N5O=779.27) 213 m/z= 779.88 (C55H33N5O=779.27) 214 m/z= 779.88 (C55H33N5O=779.27) 215 m/z= 755.86 (C53H33N5O=755.27) 216 m/z= 755.86 (C53H33N5O=755.27) 217 m/z=694.73 (C47H26N4O3=694.20) 218 m/z=744.79 (C51H28N4O3=744.22) 219 m/z=744.79 (C51H28N4O3=744.22) 220 m/z=744.79 (C51H28N4O3=744.22) 221 m/z=744.79 (C51H28N4O3=744.22) 222 m/z=744.79 (C51H28N4O3=744.22) 223 m/z=744.79 (C51H28N4O3=744.22) 224 m/z = 770.83 (C53H30N4O3 = 770.23) 225 m/z=770.83 (C53H30N4O3=770.23) 226 m/z=593.70 (C40H23N3OS=593.16) 227 m/z=643.75 (C44H25N3OS=643.17) 228 m/z=643.75 (C44H25N3OS=643.17) 229 m/z=643.75 (C44H25N3OS=643.17) 230 m/z=643.75 (C44H25N3OS=643.17) 231 m/z=643.75 (C44H25N3OS=643.17) 232 m/z=643.75 (C44H25N3OS=643.17) 233 m/z = 669.79 (C46H27N3OS = 669.19) 234 m/z=669.79 (C46H27N3OS=669.19) 235 m/z = 728.84 (C52H32N4O=728.26) 236 m/z= 778.90 (C56H34N4O=778.27) 237 m/z= 778.90 (C56H34N4O=778.27) 238 m/z= 778.90 (C56H34N4O=778.27) 239 m/z= 778.90 (C56H34N4O=778.27) 240 m/z= 778.90 (C56H34N4O=778.27) 241 m/z= 778.90 (C56H34N4O=778.27) 242 m/z = 804.93 (C58H36N4O=804.29) 243 m/z = 804.93 (C58H36N4O=804.29) 244 m/z=667.71 (C46H25N3O3=667.19) 245 m/z=717.77 (C50H27N3O3=717.21) 246 m/z=717.77 (C50H27N3O3=717.21) 247 m/z=717.77 (C50H27N3O3=717.21) 248 m/z=717.77 (C50H27N3O3=717.21) 249 m/z=717.77 (C50H27N3O3=717.21) 250 m/z=717.77 (C50H27N3O3=717.21) 251 m/z=743.80 (C52H29N3O3=743.22) 252 m/z=743.80 (C52H29N3O3=743.22) 253 m/z=643.75 (C44H25N3OS=643.17) 254 m/z=693.81 (C48H27N3OS=693.19) 255 m/z=693.81 (C48H27N3OS=693.19) 256 m/z=693.81 (C48H27N3OS=693.19) 257 m/z=693.81 (C48H27N3OS=693.19) 258 m/z=693.81 (C48H27N3OS=693.19) 259 m/z=693.81 (C48H27N3OS=693.19) 260 m/z=719.85 (C50H29N3OS=719.20) 261 m/z=719.85 (C50H29N3OS=719.20) 262 m/z=692.76 (C48H28N4O2=692.22) 263 m/z=742.82 (C52H30N4O2=742.24) 264 m/z=742.82 (C52H30N4O2=742.24) 265 m/z=742.82 (C52H30N4O2=742.24) 266 m/z=742.82 (C52H30N4O2=742.24) 267 m/z=742.82 (C52H30N4O2=742.24) 268 m/z=742.82 (C52H30N4O2=742.24) 269 m/z=768.86 (C54H32N4O2=768.25) 270 m/z=768.86 (C54H32N4O2=768.25) 271 m/z=683.77 (C46H25N3O2S=683.17) 272 m/z=683.77 (C46H25N3O2S=683.17) 273 m/z=683.77 (C46H25N3O2S=683.17) 274 m/z=683.77 (C46H25N3O2S=683.17) 275 m/z=683.77 (C46H25N3O2S=683.17) 276 m/z=683.77 (C46H25N3O2S=683.17) 277 m/z=709.81 (C48H27N3O2S=709.18) 278 m/z=709.81 (C48H27N3O2S=709.18) 279 m/z= 643.75 (C44H25N3OS= 643.17) 280 m/z= 643.75 (C44H25N3OS= 643.17) 281 m/z= 719.85 (C50H29N3OS= 719.20) 282 m/z= 719.85 (C50H29N3OS= 719.20) 283 m/z = 693.81 (C48H27N3OS = 693.19) 284 m/z = 693.81 (C48H27N3OS = 693.19) 285 m/z = 759.87 (C52H29N3O2S = 759.2) 286 m/z = 775.94 (C52H29N3OS2 = 775.18) 287 m/z= 678.78 (C48H30N4O=678.24) 288 m/z= 728.84 (C52H32N4O=728.26) 289 m/z= 728.84 (C52H32N4O=728.26) 290 m/z= 728.84 (C52H32N4O=728.26) 291 m/z= 728.84 (C52H32N4O=728.26) 292 m/z= 728.84 (C52H32N4O=728.26) 293 m/z= 728.84 (C52H32N4O=728.26) 294 m/z= 754.87 (C54H34N4O=754.27) 295 m/z= 754.87 (C54H34N4O=754.27) 296 m/z= 603.67 (C42H25N3O2= 603.19) 297 m/z = 653.73 (C46H27N3O2 = 653.21) 298 m/z = 653.73 (C46H27N3O2 = 653.21) 299 m/z = 653.73 (C46H27N3O2 = 653.21) 300 m/z = 653.73 (C46H27N3O2 = 653.21) 301 m/z = 653.73 (C46H27N3O2 = 653.21)

compound ¹ H NMR (CDCl ₃ , 200 Mz) One δ = 8.43 (1H, dd), 8.28 (4H, dd), 7.94 (1H, dd), 7.89 (1H, dd), 7.70 to 7.66 (5H, m), 7.51 (4H, t), 7.41 to 7.25 ( 8H, m) 4 δ = 8.51(1H, m), 8.43(1H, d), 8.28(4H, d), 8.16(1H, m), 7.88(2H, m), 7.70~7.66(7H, m), 7.51(4H, t), 7.41~7.32 (6H, m) 9 δ = 8.28 (4H, d), 8.18 (1H, d), 8.00 (1H, d), 7.89 (1H, d), 7.77 (1H, s), 7.68 (5H, m), 7.52 to 7.32 (15H, m) 28 δ = 8.54(1H, m), 8.45(1H, m), 8.28(2H, d), 8.16(1H, m), 7.96(3H, m), 7.84(3H, m), 7.68(4H, m) , 7.52~7.25 (15H, m) 34 δ = 8.44(1H, m), 8.28(2H, d), 8.16(2H, d), 7.98~7.82(6H, m), 7.67(2H, m), 7.53~7.25(16H, m) 48 δ = 8.74 (1H, d), 8.45 (1H, d), 8.28 (4H, d), 8.16 (2H, m), 7.96 (2H, m), 7.82 (1H, d), 7.67 to 7.25 (20H, m) 73 δ = 8.74 (2H, d), 8.28 (4H, d), 7.92 (3H, m), 7.75 (1H, d), 7.62 to 7.25 (19H, m) 99 δ = 8.28 (4H, d), 8.18 (1H, d), 8.02 (3H, m), 7.89 (1H, d), 7.75 (3H, dt), 7.62 (1H, d), 7.52 to 7.41 (15H, m) 107 δ = 8.74(1H, dd), 8.28(4H, d), 8.18(1H, dd), 8.00(1H, d), 7.94(1H, dd), 7.89(1H, d), 7.75(3H, dt) , 7.58~7.25 (21H, m) 210 δ = 9.09(1H, s), 8.74(1H, dd), 8.49(1H, dd), 8.28(2H, d), 8.16(2H, m), 8.00 to 7.81(7H, m), 7.67 to 7.25( 19H, m) 220 δ = 8.51(1H, m), 8.43(1H, d), 8.28(2H, d), 8.16(1H, m), 7.85(7H, m), 7.68(6H, m), 7.51~7.32(10H, m) 225 δ = 8.28 (2H, d), 8.18 (1H, d), 8.00 (1H, d), 7.89 to 7.77 (7H, m), 7.68 (4H, m), 7.52 to 7.32 (15H, m) 226 δ = 8.43(1H, d), 8.16(1H, d), 8.05(1H, m), 7.96(2H, m), 7.82(7H, m), 7.66(1H, d), 7.58~7.25(10H, m) 242 δ = 8.74(1H, d), 8.30(2H, d), 8.17(2H, m), 8.00(1H, d), 7.94(1H, m), 7.81(8H, m), 7.66(1H, d) , 7.58~7.25 (20H, m) 244 δ = 8.43 (1H, d), 8.16 (1H, d), 7.94 (1H, d), 7.89 to 7.58 (13H, m), 7.38 to 7.25 (9H, m) 260 δ = 8.43 (1H, d), 8.34 (1H, s), 8.16 (1H, d), 8.00 to 7.81 (12H, m), 7.66 to 7.25 (14H, m) 262 δ = 8.74 (2H, d), 7.94 (2H, d), 7.82 (4H, m), 7.70 to 7.25 (20H, m) 270 δ = 8.74 (1H, d), 8.18 (1H, d), 7.94 (1H, d), 7.85 (1H, m), 8.00 to 7.77 (5H, m), 7.70 to 7.25 (23H, m) 271 δ = 8.54 (1H, d), 8.16 (1H, m), 8.05 to 7.66 (14H, m), 7.52 to 7.32 (9H, m) 287 δ = 8.74 (2H, d), 8.23 (1H, s), 7.94 (2H, d), 7.81 to 7.25 (25H, m) 299 δ = 8.51(1H, dd), 8.43(1H, d), 8.28(2H, dd), 8.23(1H, s), 8.16(1H, m), 7.88~7.66(11H, m), 7.51~7.32( 10H, m)

< Experimental example >

1) Fabrication of an organic light emitting device

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and then treated with UVO (ultravioletozone) for 5 minutes using UV in a UV (ultraviolet) cleaner. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

A hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and a hole transport layer NPB (N,N'-diphenyl- (1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. For the light emitting layer, 500 Å of one compound described in Formula 1 was deposited as a host as shown in Table 5 below, and a red phosphorescent dopant was deposited by _{doping 3% of (piq) 2} Ir(acac). After that, 60Å of BCP was deposited as a hole blocking layer, and Alq _{3 as an electron transport layer thereon} was deposited at 200 Å. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under ^{10 -6} to 10 ^{-8 torr for each material and used for OLED manufacturing.}

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured.

light emitting layer
compound drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 A 5.49 12.5 0.672, 0.309 41 Comparative Example 2 B 5.41 11.9 0.679, 0.321 45 Comparative Example 3 C 5.13 11.7 0.673, 0.311 57 Comparative Example 4 D 5.35 12.5 0.681, 0.317 55 Example 1 One 4.36 24.7 0.687, 0.329 71 Example 2 3 4.21 21.3 0.683, 0.320 63 Example 3 7 4.17 22.1 0.675, 0.323 67 Example 4 17 4.29 22.8 0.688, 0.311 66 Example 5 18 4.31 25.0 0.680, 0.315 58 Example 6 21 4.22 23.7 0.675, 0.320 63 Example 7 26 4.28 24.0 0.683, 0.309 59 Example 8 35 4.30 20.2 0.672, 0.316 72 Example 9 45 4.27 21.1 0.681, 0.310 69 Example 10 61 4.19 19.8 0.678, 0.328 84 Example 11 66 4.07 18.5 0.688, 0.312 88 Example 12 100 4.39 17.2 0.673, 0.307 93 Example 13 104 4.20 16.8 0.679, 0.321 87 Example 14 107 4.18 18.0 0.681, 0.313 93 Example 15 108 4.21 16.5 0.679, 0.326 86 Example 16 115 4.28 17.8 0.683, 0.322 84 Example 17 120 4.14 15.3 0.684, 0.318 76 Example 18 143 4.15 21.6 0.678, 0.328 77 Example 19 148 4.20 20.3 0.685, 0.324 76 Example 20 163 3.91 14.7 0.677, 0.328 60 Example 21 174 4.02 14.9 0.684, 0.312 58 Example 22 176 3.94 14.0 0.672, 0.318 53 Example 23 188 3.87 14.6 0.681, 0.313 55 Example 24 189 3.96 14.6 0.676, 0.328 57 Example 25 218 4.28 17.3 0.679, 0.327 94 Example 26 231 4.25 18.2 0.670, 0.320 86 Example 27 242 4.35 17.6 0.673, 0.329 83 Example 28 251 4.10 15.3 0.687, 0.318 56 Example 29 262 4.07 14.9 0.682, 0.311 56 Example 30 265 4.13 15.0 0.671, 0.317 60 Example 31 272 4.32 17.0 0.679, 0.325 78 Example 32 298 4.34 20.7 0.684, 0.327 74

2) Fabrication of organic light emitting device

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and then treated with UVO (ultravioletozone) for 5 minutes using UV in a UV (ultraviolet) cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal deposition equipment for organic deposition.

A hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and a hole transport layer NPB (N,N'-diphenyl- (1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. For the light emitting layer, as a host, one compound described in Formula 1 and one compound described in Table 6 were pre-mixed and deposited at 500 Å in one park after pre-mixing, and the red phosphorescent dopant was (piq) ₂ Ir (acac) 3 % doped and deposited. After that, 60Å of BCP was deposited as a hole blocking layer, and Alq _{3 as an electron transport layer thereon} was deposited at 200 Å. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under ^{10 -6} to 10 ^{-8 torr for each material and used for OLED manufacturing.}

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured.

light emitting layer
compound ratio
(P:N) drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 5 One 0:1 4.36 24.7 0.687, 0.329 71 Comparative Example 6 45 0:1 4.27 21.1 0.681, 0.310 69 Comparative Example 7 100 0:1 4.39 17.2 0.673, 0.307 93 Comparative Example 8 188 0:1 3.87 14.6 0.681, 0.313 55 Comparative Example 9 272 0:1 4.32 17.0 0.679, 0.325 78 Example 33 host A : 1 3:1 4.31 43.2 0.680, 0.315 130 Example 34 2:1 4.39 44.5 0.673, 0.307 167 Example 35 1:1 4.20 46.7 0.679, 0.321 198 Example 36 1:2 4.18 47.0 0.681, 0.313 203 Example 37 host B: 45 3:1 4.13 29.8 0.679, 0.326 198 Example 38 2:1 4.10 30.9 0.677, 0.328 133 Example 39 1:1 4.05 31.3 0.684, 0.312 157 Example 40 1:2 4.04 32.0 0.672, 0.318 180 Example 41 host C:100 3:1 4.35 35.7 0.681, 0.313 242 Example 42 2:1 4.32 34.3 0.676, 0.328 288 Example 43 1:1 4.38 33.5 0.679, 0.327 331 Example 44 1:2 4.35 33.9 0.670, 0.320 355 Example 45 host D:188 3:1 4.17 27.1 0.673, 0.329 101 Example 46 2:1 4.14 28.0 0.687, 0.318 126 Example 47 1:1 4.04 29.5 0.682, 0.311 140 Example 48 1:2 4.03 30.7 0.671, 0.317 141 Example 49 host E:272 3:1 4.32 32.1 0.679, 0.325 262 Example 50 2:1 4.34 33.2 0.684, 0.327 287 Example 51 1:1 4.27 34.8 0.680, 0.326 311 Example 52 1:2 4.29 33.7 0.682, 0.325 330

As can be seen from the results of Table 5, the organic electroluminescent device using the organic electroluminescent device light emitting layer material of the present invention has a lower driving voltage, improved luminous efficiency, and significantly improved lifespan compared to Comparative Examples 1 to 4 could check

In addition, looking at the results of Table 6, when the compound of Formula 1 (n type) and the compound of Formula A according to the present application are included at the same time, better efficiency and lifespan effect are exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan. In the present invention, it was confirmed that when the donor role was the compound of Formula A, and the acceptor role was the compound of Formula 1 used as the light emitting layer host, excellent device characteristics were exhibited.

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 (12)

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

In Formula 1,
X is O; or S;
N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,
L and L1 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group, a and d are integers of 1 to 4,
Y is O; S; CR _x R _y ; or NR _z ,
R ₁ to R ₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle, and b is an integer of 1 to 4 and c is an integer from 1 to 3,
The b+c ≤ 6,
The R _x , R _y and R _z are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
Each substituent is the same as defined in Formula 1,
1A to 1D and 1A' to 1D' refer to the bonding positions of the substituents, respectively,
In Formula 2, when -(L)aN-Het is bonded to 1A', the

binds to any one of 1A, 1C and 1D. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 4 to 8:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 4 to 8,
The definition of each substituent is the same as the definition in Formula 1 above. The method according to claim 1, wherein the formula 1

is a heterocyclic compound represented by the following 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 above. The method according to claim 1, wherein the formula 1

is a heterocyclic compound represented by any one of the following formulas 2-1 to 2-5:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
The definitions of Y, L1 and d are the same as those in Formula 1 above,
Ar is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group. The heterocyclic compound of claim 1, wherein Formula 1 is any one of the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the heterocyclic compound according to any one of claims 1 to 6 phosphorus organic light emitting device. The organic light-emitting device of claim 7 , wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound. The organic light-emitting device of claim 7 , wherein the organic material layer includes an emission layer, the emission layer includes a host material, and the host material includes the heterocyclic compound. The organic light-emitting device of claim 7 , wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound. The organic light-emitting device of claim 7 , wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound. The method according to claim 7, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. An organic light-emitting device that further comprises one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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