KR20220152420A - Organic light emitting device, heterocyclic compound, and composition for organic material layer of organic light emitting device - Google Patents

Abstract

The present invention relates to an organic light emitting element, a heterocyclic compound, a composition for an organic material layer of an organic light emitting element, and a manufacturing method of the organic light emitting element. The organic light emitting element comprises a first electrode, a second electrode and organic material layers having at least one layer installed between the first electrode and the second electrode. Therefore, the organic light emitting element can lower a driving voltage and increase light efficiency and lifetime.

Description

Organic light emitting device, heterocyclic compound, composition for organic material layer of organic light emitting device, and manufacturing method of organic light emitting device

The present specification relates to an organic light emitting device, a heterocyclic compound, and a composition for an organic material layer of an organic light emitting device.

The electroluminescent device is a type of self-luminous display device, and has advantages such as 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 voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as needed.

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

In order to improve the performance, lifespan or efficiency of organic light emitting devices, the development of materials for organic thin films is continuously required.

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

An object of the present specification is to provide an organic light emitting device, a heterocyclic compound, a composition for an organic material layer of an organic light emitting device, and a manufacturing method of the organic light emitting device.

In one embodiment of the present specification, the first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Formula 1 below. do.

[Formula 1]

In Formula 1,

X and Y are each independently CRR'; O; or S,

Z1 to Z3 are each independently N; Or CR", at least one of Z1 to Z3 is N,

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

l1 is an integer from 1 to 5;

When l1 is 2 or more, L are the same as or different from each other,

Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group,

Ar3, R, R', R", R1 and R2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

a is an integer from 1 to 7;

r1 is an integer from 0 to 6;

r2 is an integer from 0 to 4;

When a, r1 and r2 are each 2 or more, each of Ar2, R1 and R2 is the same as or different from each other,

When a is an integer from 1 to 5, Ar3 is the same as or different from each other.

In another embodiment, the heterocyclic compound of Formula 1 is provided.

In another exemplary embodiment, a composition for an organic material layer of an organic light emitting device including the heterocyclic compound of Chemical Formula 1 is provided.

The organic light emitting device described herein includes one heterocyclic compound of Formula 1 or a heterocyclic compound of Formula 1 and a compound of Formula 2 in some organic material layers, thereby lowering the driving voltage of the device, improving light efficiency, and life characteristics can be improved. In particular, the compounds of Chemical Formulas 1 and 2 may be used as a material for a light emitting layer of an organic light emitting device.

The heterocyclic compound of Chemical Formula 1 includes an aryl substituent, and thus has excellent thermal stability and luminous efficiency.

In the heterocyclic compound of the present invention, dibenzofuran/dibenzothiophene/fluorene and fused-carbazole are amphoteric substances having excellent hole and electron transport. The dibenzofuran/dibenzothiophene/fluorene and the condensed carbazole are linked by an azine (pyridine, pyrimidine, or triazine) linker, which is an electron attractor with high electron absorption. At this time, as dibenzofuran/dibenzothiophene/fluorene is substituted with an aryl group, molecular stability may be increased, and thermal stability may be significantly increased due to occurrence of steric hindrance of the compound. Therefore, as well as having a high glass transition temperature and uniform morphology, it has high crystallinity and packing density, and thus thermal stability can be further improved.

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

Hereinafter, this specification will be described in more detail.

In this specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

는 결합되는 위치를 의미한다.In this specification, the formula

means the position to be combined.

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 hydrogen atom is substituted, that is, the position where the substituent is substituted, 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, "substituted or unsubstituted" deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; A C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; A C2 to C60 heteroaryl group; silyl group; phosphine oxide group; And one or more substituents selected from the group consisting of an amine group, or two or more substituents selected from the above exemplified substituents are substituted or unsubstituted with a linked substituent.

In the present specification, "when no substituent is shown in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ² H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In an exemplary embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all possible positions of the substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be an isotope of deuterium, and in this case, the content of deuterium may be 0% to 100%.

In one embodiment of the present application, in "when no substituent is indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents explicitly exclude deuterium such as hydrogen. If not, hydrogen and deuterium may be mixed and used in the compound.

In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron composed of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or ² H.

In an exemplary embodiment of the present application, isotopes, which mean atoms having the same atomic number (Z) but different mass numbers (A), have the same number of protons, but have neutrons It can also be interpreted as an element with a different number of neutrons.

In an exemplary embodiment of the present application, the meaning of the content T% of a specific substituent is to define the total number of substituents that a base compound can have as T1, and the number of specific substituents among them is defined as T2. It can be defined as /T1×100 = T%.

로 표시되는 페닐기에 있어 중수소의 함량 20%라는 것은 페닐기가 가질 수 있는 치환기의 총 개수는 5(식 중 T1)개이고, 그 중 중수소의 개수가 1(식 중 T2)인 경우 20%로 표시될 수 있다. 즉, 페닐기에 있어 중수소의 함량이 20%인 것은 하기 구조식으로 표시될 수 있다.That is, in one example,

In the phenyl group represented by 20% of the deuterium content means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuterium is 1 (T2 in the formula), it will be represented by 20% can That is, in the phenyl group, the deuterium content of 20% can be represented by the following structural formula.

In addition, in an exemplary embodiment of the present application, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group without deuterium atoms, that is, having 5 hydrogen atoms.

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 of the alkyl group may be 1 to 60, specifically 1 to 40, and 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group ethyl 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-methyl A pentyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but are 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 alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically, 2 to 20. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 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 is not limited thereto.

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

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, 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. It is not limited.

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

In the present specification, the terphenyl group may be selected from the following structures.

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

,

,

,

,

,

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

,

,

,

,

,

etc., 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 group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means 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 also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40, 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, and 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, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthridi 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, A phenoxazinyl group, a phenanthridyl group, an imidazopyridinyl group, a thienyl group, an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, an indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenantrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo [c] [1,2,5] thiadiazolyl group, 2,3-dihydrobenzo [b] thiophene, 2,3-dihydrobenzofuran, 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] carbazolyl group, and the like, but are not limited thereto.

(트리메틸실릴기),

(트리에틸실릴기),

(t-부틸디메틸실릴기),

(비닐디메틸실릴기),

(프로필디메틸실릴기),

(트리페닐실릴기),

(디페닐실릴기),

(페닐실릴기) 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group is a substituent that includes Si and the Si atom is directly connected as a radical, and is represented by -Si(R101)(R102)(R103), R101 to R103 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; heterocycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. A specific example of the silyl group is

(trimethylsilyl group),

(triethylsilyl group),

(t-butyldimethylsilyl group),

(vinyldimethylsilyl group),

(propyldimethylsilyl group),

(triphenylsilyl group),

(diphenylsilyl group),

(phenylsilyl group), but is not limited thereto.

In the present specification, the phosphine oxide group is represented by -P (= O) (R104) (R105), R104 and R105 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; heterocycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the above-described examples may be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.

In the present specification, the amine group is represented by -N(R106)(R107), R106 and R107 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; heterocycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. The amine group is -NH ₂ ; monoalkylamine group; monoarylamine group; Monoheteroarylamine group; Dialkylamine group; Diaryl amine group; Diheteroarylamine group; an alkyl arylamine group; Alkylheteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, and 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, a 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene Examples include a ylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.

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

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

[Formula 1]

In Formula 1,

X and Y are each independently CRR'; O; or S,

Z1 to Z3 are each independently N; Or CR", at least one of Z1 to Z3 is N,

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

l1 is an integer from 1 to 5;

When l1 is 2 or more, L are the same as or different from each other,

Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group,

Ar3, R, R', R", R1 and R2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

a is an integer from 1 to 7;

r1 is an integer from 0 to 6;

r2 is an integer from 0 to 4;

When a, r1 and r2 are each 2 or more, each of Ar2, R1 and R2 is the same as or different from each other,

When a is an integer from 1 to 5, Ar3 is the same as or different from each other.

In one embodiment of the present specification, X and Y are CRR'; O; or S, R and R' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, X and Y are CRR'; O; or S, R and R' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, X and Y are CRR'; O; or S, R and R' are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; Or a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, X and Y are CRR'; O; or S, R and R' are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C1 to C30 alkyl group.

In one embodiment of the present specification, X and Y are CRR'; O; Or S, R and R' are each independently a substituted or unsubstituted C1 to C30 alkyl group.

In one embodiment of the present specification, X and Y are CRR'; O; Or S, R and R' are each independently a substituted or unsubstituted C1 to C10 alkyl group.

In one embodiment of the present specification, X and Y are CRR'; O; Or S, R and R' are each independently a C1 to C10 alkyl group.

In one embodiment of the present specification, X and Y are CRR'; O; or S, and R and R' are each independently a methyl group.

In one embodiment of the present specification, Z1 to Z3 are each independently N or CR", and any one of Z1 to Z3 may be N.

In one embodiment of the present specification, Z1 to Z3 are each independently N or CR", and Z1 and Z2, Z1 and Z3, or Z2 and Z3 may be N.

In one embodiment of the present specification, Z1 to Z3 are each independently N or CR", and Z1 to Z3 may be N.

In one embodiment of the present specification, R" may be hydrogen; or deuterium.

In one embodiment of the present specification, Formula 1 may be represented by Formula 1-1 or 1-2 below.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, X1 is O; or S, and the definitions of the remaining substituents are the same as those of Formula 1.

In one embodiment of the present specification, X1 may be O.

In one embodiment of the present specification, X1 may be S.

In one embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

In one embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

In one embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

In one embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C10 arylene group.

In one embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L is a direct bond; or a C6 to C30 arylene group.

In one embodiment of the present specification, L is a direct bond; or a C6 to C20 arylene group.

In one embodiment of the present specification, L is a direct bond; or a C6 to C10 arylene group.

In one embodiment of the present specification, L is a direct bond; or a phenylene group.

In one embodiment of the present specification, L is a direct bond; or selected from the following structures.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C20 aryl group.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a C6 to C20 aryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar1 and Ar2 are each independently a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, a is 1 or 2.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; Or a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a C6 to C30 aryl group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C15 aryl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or an aryl group of C6 to C15 unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Or a phenyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; Or a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, R1 and R2 are each independently hydrogen; or deuterium.

In one embodiment of the present specification, Chemical Formula 1-1 may be represented by any one of Chemical Formulas 1-1-1 to 1-1-4.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

In Chemical Formulas 1-1-1 to 1-1-4, the definition of each substituent is the same as that of Chemical Formulas 1 and 1-1.

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

[Formula 1-2-1]

[Formula 1-2-2]

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

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 is 0% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 10% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be greater than 0% and less than or equal to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 10% to 100%.

In one embodiment of the present specification, the photochemical characteristics of a compound containing no deuterium and a compound containing deuterium are almost similar, but when deposited on a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance. have.

Accordingly, when EOD (Electron Only Device) and HOD (Hole Only Device) are fabricated to check the current density according to voltage, the compound of Formula 1 according to the present application including deuterium has a much more balanced charge than the compound without deuterium. It can be confirmed that it exhibits transport characteristics.

In addition, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited on a more uniform surface without any aggregates.

In addition, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, the deuterium content of the heterocyclic compound of Formula 1 according to the present application is within the above range. As it satisfies, the stability of the entire molecule increases, which has the effect of improving the lifespan of the device.

In one embodiment of the present specification, Formula 1 may be represented by any one of the following compounds.

In one embodiment of the present specification, the organic material layer including the heterocyclic compound of Formula 1 may further include a compound of Formula 2 below.

[Formula 2]

In Formula 2,

Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

R21, R22 and R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

L21 and L22 are each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,

l21 and l22 are each an integer from 1 to 5,

When l21 and l22 are each 2 or more, each L21 and L22 are the same as or different from each other,

r21 and r22 are each an integer from 0 to 7;

When each of r21 and r22 is 2 or more, each of R21 and R22 is the same as or different from each other.

When the heterocyclic compound represented by Chemical Formula 1 is used together with the compound represented by Chemical Formula 2, it was confirmed that an organic light-emitting device exhibits more excellent effects in life, efficiency, and driving voltage characteristics. This result can be expected that an exciplex phenomenon has occurred. The exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of donor (p-host) and the LUMO level of acceptor (n-host) is released by electron exchange between two molecules of N type HOST compound and P type HOST compound. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport capability are used as the host of the light emitting layer, holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve the lifespan.

An organic light emitting device according to another exemplary embodiment of the present specification includes a first electrode; It includes a second electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer is a heterocyclic compound represented by Chemical Formula 1; And it may include the compound of formula (2).

In one embodiment of the present specification, the L21 and L22 are each independently a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

In one embodiment of the present specification, the L21 and L22 are a direct bond; Or a C6 to C30 arylene group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, the L21 and L22 are a direct bond; Or a C6 to C12 arylene group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, the L21 and L22 are a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; Or a biphenylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group, R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group, R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); 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 a substituted or unsubstituted C2 to C30 heteroaryl group, R101 to R103 are each independently hydrogen; heavy hydrogen; 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 a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group, R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); Or a substituted or unsubstituted C6 to C30 aryl group, R101 to R103 are each independently hydrogen; heavy hydrogen; C6 to C30 aryl group; or a C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); Or an aryl group of C6 to C30 unsubstituted or substituted with heavy hydrogen, R101 to R103 are each independently hydrogen; heavy hydrogen; C6 to C30 aryl group; or a C2 to C30 heteroaryl group.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted triphenylenyl group, and R101 to R103 are each independently hydrogen; heavy hydrogen; Or an aryl group of C6 to C30.

In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); Or an aryl group of C6 to C30 unsubstituted or substituted with heavy hydrogen, R101 to R103 are each independently hydrogen; heavy hydrogen; Or an aryl group of C6 to C30.

(트리페닐실릴기); 중수소 또는 시아노기로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 비페닐기; 중수소로 치환 또는 비치환된 터페닐기; 나프틸기; 9,9'-디메틸-9H-플루오레닐기; 9,9'-디페닐-9H-플루오레닐기; 9.9'-스피로비[플루오렌]; 또는 트리페닐레닐기이다.In one embodiment of the present specification, Ar21 and Ar22 are each independently a cyano group;

(triphenylsilyl group); A phenyl group unsubstituted or substituted with a deuterium or cyano group; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; naphthyl group; 9,9'-dimethyl-9H-fluorenyl group; 9,9'-diphenyl-9H-fluorenyl group; 9.9'-spirobi[fluorene]; or a triphenylenyl group.

In one embodiment of the present specification, R21 and R22 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present specification, R21 and R22 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, R21 and R22 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In one embodiment of the present specification, R21 and R22 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C10 alkyl group; A substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.

In one embodiment of the present specification, R21 and R22 are each independently hydrogen; or deuterium.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 is 0% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 is 0% or 10% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 is 0% or 30% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 may be 0%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 may be greater than 0% and less than or equal to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 may be 10% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 2 may be 100%.

In one embodiment of the present specification, Formula 2 may be represented by any one of the following compounds.

In one embodiment of the present specification, the organic material layer may include the heterocyclic compound of Formula 1 and the compound of Formula 2 in a weight ratio of 1:10 to 10:1, preferably 1:8 to 8: It may be included in a weight ratio of 1, 1:5 to 5:1, 1:3 to 3:1.

In one embodiment of the present specification, at least one of Chemical Formulas 1 and 2 may have a deuterium content greater than 0% and less than or equal to 100%.

In one embodiment of the present specification, the organic light emitting diode has i) a deuterium content of Formula 1 greater than 0% and less than or equal to 100%, and a deuterium content of Formula 2 of 0%; ii) the deuterium content of Formula 1 is 0%, and the deuterium content of Formula 2 is greater than 0% and 100% or less; and iii) deuterium content of Chemical Formulas 1 and 2 above 0% and 100% or less, respectively; Any one of them can be satisfied.

In one embodiment of the present specification, the organic material layer may further include a phosphorescent dopant.

In one embodiment of the present specification, the phosphorescent dopant may be a green, blue, or red phosphorescent dopant.

In one embodiment of the present specification, the phosphorescent dopant may be a green phosphorescent dopant.

In one embodiment of the present specification, the phosphorescent dopant may be 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 mutually different bidentate ligands, and M is a metal forming an octahedral complex.

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

L, L' and L" are anionic bidentate ligands coordinated to M with the iridium-based dopant by sp2 carbon and a hetero atom, and non-limiting examples of L, L' and L" include 1-phenylisoquinoline, 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, thiophenepyrizine, phenylpyridine, benzothione There are open pyrizine, 3-methoxy-2-phenyl pyridine, thiophen pyrizine, tolyl pyridine and the like.

X' and X" may function to trap electrons or holes, and non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate , 8-hydroxyquinolinate and the like.

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

In one embodiment of the present specification, the content of the dopant may have a content of 1% to 15%, preferably 1% to 10%, more preferably 1% to 5% based on the entire light emitting layer.

An organic light emitting device according to an exemplary embodiment of the present specification is a method and material for manufacturing a typical organic light emitting device, except that one or more organic material layers are formed using the above-described heterocyclic compound of Formula 1 and the compound of Formula 2. can be manufactured by

The heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 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 means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, and the like as organic material layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

In one 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 cathode, and the second electrode may be an anode.

In the organic light emitting device of the present specification, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound represented by Chemical Formula 1.

In the organic light emitting device of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer may include the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2.

In the organic light emitting device of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a host, and the host may include the heterocyclic compound represented by Chemical Formula 1.

In the organic light emitting device of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a host, and the host may include the heterocyclic compound of Formula 1 and the compound of Formula 2.

When a host is constructed by combining the heterocyclic compound of Formula 1 and the compound of Formula 2, efficiency and lifespan are better than when one host is used.

In one embodiment of the present specification, the heterocyclic compound of Formula 1 may be used as an N-type host material, and the compound of Formula 2 may be used as a P-type host material.

In one embodiment of the present specification, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Formula 1 and the compound of Formula 2 may be used as materials for the blue organic light emitting device. For example, the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 may be included in a host material of an emission layer of a blue organic light emitting device.

In another exemplary embodiment of the present specification, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound of Formula 1 and the compound of Formula 2 may be used as materials for the green organic light emitting device. For example, the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 may be included in a host material of an emission layer of a blue organic light emitting device.

In another exemplary embodiment of the present specification, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound of Formula 1 and the compound of Formula 2 may be used as materials for the red organic light emitting device. For example, the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 may be included in a host material of an emission layer of a red organic light emitting device.

The organic light emitting device of the present invention may further include at least 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.

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 structures of organic light emitting devices known in the art may be applied to the present application as well.

According 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 shown. 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 where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, an emission 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 layers other than the light emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

The organic material layer including the heterocyclic compound of Formula 1 and the compound of Formula 2 may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present specification, materials other than the heterocyclic compound of Formula 1 and the compound of Formula 2 are exemplified below, but these are for illustration only and to limit the scope of the present application. It is not, and may be replaced with materials known in the art.

Materials having a relatively high work function may be used as the anode material, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or 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 metals, metal oxides, or conductive polymers 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are 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 described in [Advanced Material, 6, p.677 (1994)] starburst amine derivatives, such as tris(4-carbazoyl-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, a soluble conductive polymer, 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-styrenesulfonate)) or the like can be used.

As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular weight or high molecular weight materials may also be used.

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

As an 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. At this time, two or more light emitting materials may be deposited and used as separate sources or may be pre-mixed and deposited as one source. In addition, a fluorescent material can be used as a light emitting material, but 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 an anode and a cathode may be used, but materials in which a host material and a dopant material are involved in light emission may also be used.

When the host of the light emitting material is mixed and used, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, at least two materials selected from among N-type host materials and P-type host materials may be used as host materials for the light emitting layer.

An organic light emitting device according to an exemplary embodiment of the present specification may be a top emission type, a bottom emission type, or a double side emission type depending on materials used.

In another exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 is provided.

A 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.

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

In another exemplary embodiment of the present specification, a composition for an organic material layer of an organic light emitting device including the heterocyclic compound of Chemical Formula 1 is provided.

In addition, another embodiment of the present specification provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound of Formula 1 and the compound of Formula 2.

Details of the heterocyclic compound of Formula 1 and the compound of Formula 2 are the same as described above.

The weight ratio of the heterocyclic compound of Formula 1 and the compound of Formula 2 in the composition may be 1:10 to 10:1, 1:8 to 8:1, or 1:5 to 5:1. And, it may be 1:3 to 3:1, but is not limited thereto.

In one embodiment of the present specification, the composition is in the form of a simple mixture of two or more compounds, and a compound in a powder state may be mixed before forming an organic material layer of an organic light emitting device, or a compound in a liquid state at an appropriate temperature or higher. can be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

The composition may further include materials known in the art, such as solvents and additives.

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

In one embodiment of the present specification, 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 a composition for an organic material layer including the heterocyclic compound of Chemical Formula 1. It provides a method for manufacturing an organic light emitting device.

A method of manufacturing an organic light emitting device according to another exemplary embodiment includes 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 a composition for an organic material layer including the heterocyclic compound of Formula 1 and the compound of Formula 2. and forming the organic material layer, wherein the forming of the organic material layer comprises a heterocyclic compound of Chemical Formula 1; And it may be formed using a thermal vacuum deposition method by pre-mixing the compound of Formula 2.

The pre-mixing (pre-mixed) means that the materials are first mixed and mixed in one park before depositing the heterocyclic compound of Formula 1 and the compound of Formula 2 on the organic layer.

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

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

[Preparation Example 1] Preparation of compound 1-1

(1) Preparation of intermediate 1-1-1

5,7-Dihydro-7,7-dimethyl-indeno[2,1-b]carbazole (5,7-Dihydro-7,7-dimethyl-indeno[2,1-b]carbazole) After [B] (31g, 109.5mmol) was added, 500ml of tetrahydrofurane (THF) was added. After lowering the reaction temperature to -78°C, n-BuLi (57ml, 142.2mmol) was added thereto, followed by stirring for 30 minutes. After that, 2,4-dichloro-6-phenyl-1,3,5-triazine [A] (25 g, 109.5 mmol) was added. After stirring for 1 hour. After completion of the reaction, the resulting solid was washed with distilled water and methanol (MeOH) to obtain intermediate 1-1-1. (26 g, yield 61.8%)

(2) Preparation of compound 1-1

To the reaction flask, intermediate 1-1-1 (9 g, 19 mmol), 4,4,5,5-tetramethyl-2- (1-phenyldibenzofuran-4-yl) -1,3,2-dioxabo Loran (4,4,5,5-tetramethyl-2-(1-phenyldibenzofuran-4-yl)-1,3,2-dioxaborolane) [C] (7g, 19mmol), Pd(PPh ₃ ) ₄ (Tetra After adding kiss(triphenylphosphine)palladium(0) (1g, 0.95mmol), K ₂ CO ₃ (potassium carbonate) (5.1g, 38mmol) and 1,4-dioxane/water (100ml/20ml) , and refluxed at 120° C. for 3 hours. After completion of the reaction, the temperature was lowered to room temperature, and the formed solid was washed with distilled water and MeOH to obtain Compound 1-1. (9 g, yield 69%)

In Preparation Example 1, Compound A of Table 1 was used instead of 2,4-dichloro-6-phenyl-1,3,5-triazine [A] , and 5,7-dihydro-7,7-dimethyl- Compound B of Table 1 is used instead of indeno[2,1-b]carbazole [B], and 4,4,5,5-tetramethyl-2-(1-phenyldibenzofuran-4-yl) Compound D was synthesized in the same manner as in Preparation Example 1, except that Compound C of Table 1 was used instead of -1,3,2-dioxaborolane [C] .

[Table 1]

[Preparation Example 2] Preparation of compound 4-1

1) Preparation of Intermediate 4-1-1

In the reaction flask, 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole [E] (15 g, 52.9 mmol), 1-bromo-3-iodobenzene [F] (17.9 g, 63.5 mmol), Pd(OAc) ₂ (palladium(II) acetate) ( 0.59g, 2.64mmol), Xantphos (3g, 5.29mmol), and NaOtBu (7.6g, 79.3mmol) were added, and 150mL of toluene was added, followed by refluxing at 120° C. for 8 hours. Upon completion of the reaction, the mixture was extracted with methylene chloride (MC) and H ₂ O, followed by column purification to obtain intermediate 4-1-1. (18 g, yield 78%)

2) Preparation of Intermediate 4-1-2

Intermediate 4-1-1 (18g, 41mmol), bis(pinacolate)diboron (20.8g, 82.1mmol), Pd(dppf)Cl ₂ ([1,1′-bis( After diphenylphosphino) ferrocene] dichloropalladium (II) (3 g, 4.1 mmol) and KOAc (12 g, 123 mmol) were added, 180 ml of 1,4-dioxane was added and refluxed at 120 ° C. for 4 hours. After the reaction was completed, extraction was performed using MC and H ₂ O, and the organic layer was concentrated and purified by column to obtain intermediate 4-1-2. (17 g, yield 85%)

3) Preparation of Compound G

2,4-dichloro-6-phenyl-1,3,5-triazine (2,4-dichloro-6-phenyl-1,3,5-triazine) (10g, 44.2mmol),4,4,5, 5-tetramethyl-2- (1-phenyldibenzo [b, d] furan-4-yl) -1,3,2-dioxaborolane (4,4,5,5-tetramethyl-2-( 1-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane) (19.6g, 53mmol), Pd(PPh ₃ ) ₄ (2.5g, 2.21mmol), K ₂ CO ₃ (18.3 g, 132.6mmol) was added, and then THF:H ₂ O=100mL:20mL was added and reacted at 85°C for 4 hours.

After the reaction was completed, the precipitated solid was washed with MeOH to obtain compound G. (17 g, yield 89%)

4) Preparation of Compound 4-1

After adding Intermediate 4-1-2 (10g, 20mmol), Compound G (10.7g, 24.7mmol), Pd(PPh ₃ ) ₄ (1.1g, 1mmol), K ₂ CO ₃ (8.3g, 60mmol), 1, 4-dioxane: H ₂ O = 100 mL: 20 mL was added and refluxed at 120° C. for 4 hours. After completion of the reaction, the resulting solid was washed with MeOH, H ₂ O, and acetone and filtered to obtain compound 4-1. (13 g, yield 86%)

In Preparation Example 2, Compound E of Table 2 was used instead of 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole [E] , and 1-bromo-3-io The target compound H was synthesized in the same manner as in Preparation Example 2, except that Compound F of Table 2 was used instead of dobenzene [F] , and Compound G-1 of Table 2 was used instead of Compound G.

[Table 2]

<Preparation Example 3> Synthesis of Compound A-3

3-bromo-1,1'-biphenyl (3-bromo-1,1'-biphenyl) 3.7g (15.8mM), 9-phenyl-9H,9'H-3,3'-bicarbazole ( 9-phenyl-9H,9'H-3,3'-bicarbazole) 6.5 g (15.8 mM), CuI 3.0 g (15.8 mM), trans-1,2-diaminocyclohxane ) 1.9mL (15.8mM) and 3.3g (31.6mM) of K ₃ PO ₄ were dissolved in 100mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added and extracted at room temperature. The organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane = 1:3) and recrystallized from methanol to obtain compound A-3. (7.5 g, yield 85%)

In Preparation Example 3, Compound A-1 of Table 3 was used instead of 3-bromo-1,1'-biphenyl, and the following instead of 9-phenyl-9H,9'H-3,3'-bicarbazole Compound C-1 of Table 3 below was synthesized by preparing in the same manner as in Preparation Example 3, except that Compound B-1 of Table 3 was used.

[Table 3]

Compounds were prepared in the same manner as in the above preparations, and the synthesis confirmation results are shown in Tables 4 and 5 below. Table 4 is an NMR value, and Table 5 is a measured value of FD-MS (Field desorption mass spectrometry).

compound ¹ H NMR (CDCl ₃ , 300 Mz) 1-1 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 2H), 7.94-7.79 (m, 6H), 7.69-7.61 (m, 2H), 7.51-7.24 (m, 13H), 1.72(s, 6H) 1-2 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 1H), 7.94-7.89 (m, 2H), 7.79 (m, 2H), 7.66-7.24 (m, 18H), 1.72 ( m, 6H) 1-3 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 1H), 7.94-7.89 (m, 2H), 7.69-7.24 (m, 20H), 1.72 (s, 6H) 1-4 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 1H), 7.94 (m, 1H), 7.85-7.81 (m, 3H), 7.61 (m, 1H), 7.51-7.24 ( m, 9H), 1.72(s, 6H) 1-9 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 1H), 7.94 (m, 1H), 7.85-7.81 (m, 3H), 7.61 (m, 1H), 7.51-7.24 ( m, 9H), 1.72(s, 6H) 1-18 δ = 8.55 (m, 1H), 8.24 (m, 1H), 8.09 (m, 1H), 7.94-7.89 (m, 2H), 7.79 (m, 2H), 7.69-7.24 (m, 22H), 1.72 ( m, 6H) 1-22 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 1H), 7.94-7.79 (m, 2H), 7.79-7.24 (m, 24H), 1.76 (s, 6H) 1-82 δ = 8.55 (m, 1H), 8.45 (m, 1H), 8.28 (m, 2H), 8.09-7.94 (m, 4H), 7.79-7.77 (m, 3H), 7.69 (m, 1H), 7.61 ( m, 1H), 7.52-7.24 (m, 13H), 1.72 (m, 6H) 1-113 δ = 8.28 (m, 2H), 7.87-7.79 (m, 6H), 7.51-7.38 (m, 12H), 1.72 (m, 6H) 1-122 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.09 (m, 2H), 7.94 (m, 2H), 7.87-7.69 (m, 6H), 7.61-7.24 (m, 15H), 1.72 ( s, 12H) 1-124 δ = 8.55 (m, 1H), 8.28 (m, 2H), 8.12-8.09 (m, 2H), 7.94 (m, 1H), 7.87-7.82 (m, 2H), 7.73 (m, 1H), 7.55- 7.24(m, 18h), 1.72(s, 12H) 2-2 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (d, 2H), 7.98-7.86 (m, 4H), 7.79-7.78 (m, 3H), 7.66-7.25 (m, 15H) 2-41 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.89 (m, 8H), 7.66-7.25 (m, 14H) 2-42 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.89 (m, 4H), 7.79 (m, 2H), 7.66-7.25 (m, 16H) 2-43 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.94 (m, 4H), 7.66-7.25 (m, 18H) 2-44 δ = 8.55 (d, 1H), 8.45 (d, 1h), 8.05-7.81 (m, 6H), 7.66-7.25 (m, 16H) 2-54 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.94 (m, 3H), 7.75-7.71 (m, 3H), 7.60-7.25 (m, 15H) 2-62 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.94 (m, 4H), 7.79-7.75 (m, 3H), 7.64-7.25 (m, 19H) 2-79 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05 (d, 1H), 7.98-7.94 (m, 2H), 7.87-7.81 (m, 3H), 7.72- 7.71(m, 2H), 7.60-7.25(m, 18H) 2-85 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 7.98-7.95 (m, 4H), 7.86 (s, 1H), 7.78-7.75 (m, 3H), 7.64 ( s, 2H), 7.51-7.25 (m, 12H) 2-166 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.08-7.99 (m, 6H), 7.82-7.77 (m, 4H), 7.60-7.25 (m, 16H) 2-199 δ = 8.28 (m, 2H), 7.85-7.81 (m, 3H), 7.72-7.71 (m, 2H), 7.51-7.38 (m, 9H) 3-30 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.95-7.89 (m, 3H), 7.79-7.75 (m, 3H), 7.66-7.25 (m, 21H) 3-41 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.79 (m, 8H), 7.66 (m, 2H), 7.53-7.25 (m, 13H) 3-42 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.89 (m, 4H), 7.79 (m, 2H), 7.53-7.25 (m, 17H) 3-58 δ = 8.55 (d, 1H), 8.24 (m, 1H), 7.94-7.89 (m, 4H), 7.79 (m, 2H), 7.66-7.25 (m, 22H) 3-66 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.79 (m, 9H), 7.66-7.64 (m, 2H), 7.51-7.25 (m, 16H) 3-81 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.79 (m, 7H), 7.66 (m, 2H), 7.51-7.25 (m, 14H) 3-112 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.91 (m, 1H), 7.79-7.75 (m, 5H), 7.66-7.25 (m, 20H) 3-122 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.89 (m, 4H), 7.79 (m, 2H), 7.66-7.25 (m, 16H), 7.13 (m, 1H) 3-123 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.89 (m, 4H), 7.66-7.25 (m, 18H), 7.13 (m, 1H) 3-163 δ = 8.55 (d, 1H), 8.45 (m, 1H), 8.28 (m, 2H), 8.04-7.89 (m, 5H), 7.77 (d, 1H), 7.51 (m, 1H), 7.53-7.25 ( m, 15H) 3-166 δ = 8.55 (d, 1H), 8.28 (m, 2H), 8.11-8.04 (m, 3H), 7.94-7.77 (m, 7H), 7.66 (m, 1H), 7.52-7.25 (m, 16H) 4-1 δ = 8.55 (d, 1H), 8.28 (m, 3H), 8.09 (m, 2H), 7.94-7.79 (m, 6H), 7.69-7.61 (m, 2H), 7.51-7.24 (m, 16H), 1.72(s, 6H) 4-2 δ = 8.55 (d, 1H), 8.28 (d, 2H), 8.09 (m, 1H), 7.94 (m, 1H), 7.79 (m, 4H), 7.66-7.24 (m, 21H), 1.72 (s, 6H) 4-3 δ = 8.55 (d, 1H), 8.28 (d, 2H), 8.09 (m, 1H), 7.94-7.89 (m, 2H), 7.79 (m, 2H), 7.66-7.25 (m, 21H), 1.72 ( s, 6H) 4-33 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 3h), 8.09 (s, 1H), 7.98-7.78 (m, 9H), 7.66 (d, 1H), 7.52-7.25 ( m, 14H) 4-34 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 7.98-7.78 (m, 9H), 7.68-7.25 (m, 17H) 4-40 δ = 8.55 (d, 1H), 8.45 (d, 1h), 8.28 (m, 3H), 8.09 (s, 1H), 7.98-7.95 (m, 3H), 7.86-7.71 (m, 6H), 7.86- 7.71(m, 6H), 7.64(s, 1H), 7.52-7.25(m, 9H) 4-51 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.89 (m, 4H), 7.79 (m, 4H), 7.66-7.25 (m, 18H) 4-55 δ = 8.55 (d, 1H), 8.45 (d, 1H), 8.28 (m, 2H), 8.05-7.94 (m, 3H), 7.85-7.25 (m, 23H) 4-106 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.95-7.66 (m, 13H), 7.51-7.25 (m, 14H) 4-113 δ = 8.55 (d, 1H), 8.28 (m, 2H), 7.94-7.79 (m, 11H), 7.68-7.66 (m, 3H), 7.53-7.25 (m, 17H) 4-128 δ = 8.55 (d, 1H), 8.28 (m, 3H), 8.09 (s, 1H), 7.94-7.89 (m, 3H), 7.71-7.64 (m, 6H), 7.51-7.25 (m, 11H) A-3 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (4H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m) ) A-4 δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (8H, m), 7.77-7.75 (3H, m), 7.62-7.35 (11H, m) ), 7.20-7.16 (2H, m) A-7 δ = 8.55 (1H, d), 8.31-8.30 (3H, d), 8.19-8.13 (2H, m), 7.99-7.89 (5H, m), 7.77-7.75 (5H, m), 7.62-7.35 (14H , m), 7.20-7.16 (2H, m) A-16 δ = 8.93–8.90 (3H, d), 8.55 (1H, d), 8.18–8.10 (5H, m), 8.00–7.77 (10H, m), 7.58–7.45 (8H, m), 7.33–7.29 (2H) , m) A-31 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (4H, m), 7.99-7.89 (4H, m), 7.77-7.35 (20H, m), 7.20-7.16 (2H, m) ) A-32 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (8H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m) ) A-34 δ = 8.55 (1H, d), 8.18–8.09 (3H, m), 8.00–7.94 (2H, m), 7.87 (1H, d), 7.79–7.77 (4H, m), 7.69–7.63 (4H, m) ), 7.51-7.25 (21H, m) A-42 δ = 8.55 (1H, d), 8.18–8.12 (2H, m), 8.00–7.87 (3H, m), 7.79–7,77 (6H, m), 7.69–7.63 (6H, m), 7.52–7.25 (14H, m) A-97 δ = 8.55 (1H, d), 8.18–8.09 (3H, m), 8.00–7.94 (2H, m), 7.87 (1H, d), 7.79–7.77 (4H, m), 7.57–7.29 (25H, m) )

compound FD-Mass compound FD-Mass 1-1 m/z= 680.79 (C48H32N4O=680.26) 1-2 m/z= 680.79 (C48H32N4O=680.26) 1-3 m/z= 680.79 (C48H32N4O=680.26) 1-4 m/z= 680.79 (C48H32N4O=680.26) 1-5 m/z= 679.81 (C49H33N3O=679.26) 1-6 m/z= 679.81 (C49H33N3O=679.26) 1-7 m/z= 679.81 (C49H33N3O=679.26) 1-8 m/z = 685.82 (C48H27D5N4O=685.29) 1-9 m/z = 685.82 (C48H27D5N4O=685.29) 1-10 m/z= 679.81 (C49H33N3O=679.26) 1-11 m/z= 679.81 (C49H33N3O=679.26) 1-12 m/z= 679.81 (C49H33N3O=679.26) 1-13 m/z= 679.81 (C49H33N3O=679.26) 1-14 m/z= 679.81 (C49H33N3O=679.26) 1-15 m/z= 679.81 (C49H33N3O=679.26) 1-16 m/z= 685.82 (C48H27D5N4O=685.29) 1-17 m/z= 756.89 (C54H36N4O= 756.29) 1-18 m/z= 756.89 (C54H36N4O= 756.29) 1-19 m/z= 690.86 (C48H22D10N4O= 690.32) 1-20 m/z= 696.89 (C48H16D16N4O= 696.36) 1-21 m/z= 756.89 (C54H36N4O= 756.29) 1-22 m/z= 756.89 (C54H36N4O= 756.29) 1-23 m/z= 756.89 (C54H36N4O= 756.29) 1-24 m/z= 756.89 (C54H36N4O= 756.29) 1-25 m/z= 756.89 (C54H36N4O= 756.29) 1-26 m/z= 756.89 (C54H36N4O= 756.29) 1-27 m/z= 756.89 (C54H36N4O= 756.29) 1-28 m/z= 756.89 (C54H36N4O= 756.29) 1-29 m/z= 756.89 (C54H36N4O= 756.29) 1-30 m/z= 756.89 (C54H36N4O= 756.29) 1-31 m/z= 756.89 (C54H36N4O= 756.29) 1-32 m/z= 756.89 (C54H36N4O= 756.29) 1-33 m/z= 756.89 (C54H36N4O= 756.29) 1-34 m/z= 756.89 (C54H36N4O= 756.29) 1-35 m/z= 756.89 (C54H36N4O= 756.29) 1-36 m/z= 756.89 (C54H36N4O= 756.29) 1-37 m/z= 756.89 (C54H36N4O= 756.29) 1-38 m/z= 756.89 (C54H36N4O= 756.29) 1-39 m/z= 756.89 (C54H36N4O= 756.29) 1-40 m/z= 756.89 (C54H36N4O= 756.29) 1-41 m/z= 680.79 (C48H32N4O=680.26) 1-42 m/z= 680.79 (C48H32N4O=680.26) 1-43 m/z= 680.79 (C48H32N4O=680.26) 1-44 m/z= 680.79 (C48H32N4O=680.26) 1-45 m/z= 679.81 (C49H33N3O=679.26) 1-46 m/z= 679.81 (C49H33N3O=679.26) 1-47 m/z= 679.81 (C49H33N3O=679.26) 1-48 m/z= 685.82 (C48H27D5N4O=685.29) 1-49 m/z= 685.82 (C48H27D5N4O=685.29) 1-50 m/z= 679.81 (C49H33N3O=679.26) 1-51 m/z= 679.81 (C49H33N3O=679.26) 1-52 m/z= 679.81 (C49H33N3O=679.26) 1-53 m/z= 679.81 (C49H33N3O=679.26) 1-54 m/z= 679.81 (C49H33N3O=679.26) 1-55 m/z= 679.81 (C49H33N3O=679.26) 1-56 m/z= 685.82 (C48H27D5N4O=685.29) 1-57 m/z= 756.89 (C54H36N4O= 756.29) 1-58 m/z= 756.89 (C54H36N4O= 756.29) 1-59 m/z= 690.86 (C48H22D10N4O= 690.32) 1-60 m/z= 696.89 (C48H16D16N4O= 696.36) 1-61 m/z= 756.89 (C54H36N4O= 756.29) 1-62 m/z= 756.89 (C54H36N4O= 756.29) 1-63 m/z= 756.89 (C54H36N4O= 756.29) 1-64 m/z= 756.89 (C54H36N4O= 756.29) 1-65 m/z= 756.89 (C54H36N4O= 756.29) 1-66 m/z= 756.89 (C54H36N4O= 756.29) 1-67 m/z= 756.89 (C54H36N4O= 756.29) 1-68 m/z= 756.89 (C54H36N4O= 756.29) 1-69 m/z= 756.89 (C54H36N4O= 756.29) 1-70 m/z= 756.89 (C54H36N4O= 756.29) 1-71 m/z= 756.89 (C54H36N4O= 756.29) 1-72 m/z= 756.89 (C54H36N4O= 756.29) 1-73 m/z= 756.89 (C54H36N4O= 756.29) 1-74 m/z= 756.89 (C54H36N4O= 756.29) 1-75 m/z= 756.89 (C54H36N4O= 756.29) 1-76 m/z= 756.89 (C54H36N4O= 756.29) 1-77 m/z= 756.89 (C54H36N4O= 756.29) 1-78 m/z= 756.89 (C54H36N4O= 756.29) 1-79 m/z= 756.89 (C54H36N4O= 756.29) 1-80 m/z= 756.89 (C54H36N4O= 756.29) 1-81 m/z= 696.86 (C48H32N4S=696.23) 1-82 m/z= 696.86 (C48H32N4S=696.23) 1-83 m/z= 696.86 (C48H32N4S=696.23) 1-84 m/z= 696.86 (C48H32N4S=696.23) 1-85 m/z = 772.96 (C54H36N4S=772.27) 1-86 m/z = 772.96 (C54H36N4S=772.27) 1-87 m/z = 772.96 (C54H36N4S=772.27) 1-88 m/z = 772.96 (C54H36N4S=772.27) 1-89 m/z = 772.96 (C54H36N4S=772.27) 1-90 m/z = 772.96 (C54H36N4S=772.27) 1-91 m/z = 772.96 (C54H36N4S=727.27) 1-92 m/z = 772.96 (C54H36N4S=772.27) 1-93 m/z= 696.86 (C48H32N4S=696.23) 1-94 m/z= 696.86 (C48H32N4S=696.23) 1-95 m/z= 696.86 (C48H32N4S=696.23) 1-96 m/z= 696.86 (C48H32N4S=696.23) 1-97 m/z = 772.96 (C54H36N4S=772.27) 1-98 m/z = 772.96 (C54H36N4S=772.27) 1-99 m/z = 772.96 (C54H36N4S=772.27) 1-100 m/z = 772.96 (C54H36N4S=772.27) 1-101 m/z = 772.96 (C54H36N4S=772.27) 1-102 m/z = 772.96 (C54H36N4S=772.27) 1-103 m/z = 772.96 (C54H36N4S=772.27) 1-104 m/z = 772.96 (C54H36N4S=772.27) 1-105 m/z= 696.86 (C48H32N4S=696.23) 1-106 m/z= 696.86 (C48H32N4S=696.23) 1-107 m/z= 696.86 (C48H32N4S=696.23) 1-108 m/z = 701.89 (C48H27D5N4S =702.27) 1-109 m/z = 783.02 (C54H26D10N4S =782.33) 1-110 m/z = 788.05 (C54H21D15N4S =787.36) 1-111 m/z = 777.99 (C54H31D5N4S =777.30) 1-112 m/z = 783.02 (C54H26D10N4S =782.33) 1-113 m/z = 766.95 (C54H26D10N4O =766.35) 1-114 m/z = 787.07 (C54H6D30N4O =786.48) 1-115 m/z = 766.95 (C54H26D10N4O =766.35) 1-116 m/z = 766.95 (C54H26D10N4O =766.35) 1-117 m/z = 706.95 (C48H6D26N4O =706.42) 1-118 m/z = 696.89 (C48H16D16N4O=696.26) 1-119 m/z= 696.86 (C48H32N4S=696.23) 1-120 m/z = 705.95 (C48H6D26N4O =705.42) 1-121 m/z = 706.87 (C51H38N4 = 706.31) 1-122 m/z = 706.87 (C51H38N4 = 706.31) 1-123 m/z = 706.87 (C51H38N4 = 706.31) 1-124 m/z = 706.87 (C51H38N4 = 706.31) 1-125 m/z= 782.92 (C57H42N4=782.34) 1-126 m/z= 782.92 (C57H42N4=782.34) 1-127 m/z= 782.92 (C57H42N4=782.34) 1-128 m/z= 782.92 (C57H42N4=782.34) 1-129 m/z= 782.92 (C57H42N4=782.34) 1-130 m/z= 782.92 (C57H42N4=782.34) 1-131 m/z= 782.92 (C57H42N4=782.34) 1-132 m/z= 782.92 (C57H42N4=782.34) 1-133 m/z = 706.87 (C51H38N4 = 706.31) 1-134 m/z = 706.87 (C51H38N4 = 706.31) 1-135 m/z = 706.87 (C51H38N4 = 706.31) 1-136 m/z = 706.87 (C51H38N4 = 706.31) 1-137 m/z= 782.92 (C57H42N4=782.34) 1-138 m/z= 782.92 (C57H42N4=782.34) 1-139 m/z= 782.92 (C57H42N4=782.34) 1-140 m/z= 782.92 (C57H42N4=782.34) 2-1 m/z= 670.78 (C45H26N4OS=670.18) 2-2 m/z= 670.78 (C45H26N4OS=670.18) 2-3 m/z= 670.78 (C45H26N4OS=670.18) 2-4 m/z= 670.78 (C45H26N4OS=670.18) 2-5 m/z= 670.78 (C45H26N4OS=670.18) 2-6 m/z= 670.78 (C45H26N4OS=670.18) 2-7 m/z= 670.78 (C45H26N4OS=670.18) 2-8 m/z= 675.81 (C45H21D5N4OS=675.21) 2-9 m/z= 675.81 (C45H21D5N4OS=675.21) 2-10 m/z= 670.78 (C45H26N4OS=670.18) 2-11 m/z= 670.78 (C45H26N4OS=670.18) 2-12 m/z= 670.78 (C45H26N4OS=670.18) 2-13 m/z= 670.78 (C45H26N4OS=670.18) 2-14 m/z= 670.78 (C45H26N4OS=670.18) 2-15 m/z= 670.78 (C45H26N4OS=670.18) 2-16 m/z= 675.81 (C45H21D5N4OS=675.21) 2-17 m/z = 746.88 (C51H30N4OS =746.21) 2-18 m/z = 746.88 (C51H30N4OS =746.21) 2-19 m/z = 680.84 (C45H16D10N4OS =680.25) 2-20 m/z= 686.88 (C45H10D16N4OS=686.28) 2-21 m/z = 746.88 (C51H30N4OS =746.21) 2-22 m/z = 746.88 (C51H30N4OS =746.21) 2-23 m/z = 746.88 (C51H30N4OS =746.21) 2-24 m/z = 746.88 (C51H30N4OS =746.21) 2-25 m/z = 746.88 (C51H30N4OS =746.21) 2-26 m/z = 746.88 (C51H30N4OS =746.21) 2-27 m/z = 746.88 (C51H30N4OS =746.21) 2-28 m/z = 746.88 (C51H30N4OS =746.21) 2-29 m/z = 746.88 (C51H30N4OS =746.21) 2-30 m/z = 746.88 (C51H30N4OS =746.21) 2-31 m/z = 746.88 (C51H30N4OS =746.21) 2-32 m/z = 746.88 (C51H30N4OS =746.21) 2-33 m/z = 746.88 (C51H30N4OS =746.21) 2-34 m/z = 746.88 (C51H30N4OS =746.21) 2-35 m/z = 746.88 (C51H30N4OS =746.21) 2-36 m/z = 746.88 (C51H30N4OS =746.21) 2-37 m/z = 746.88 (C51H30N4OS =746.21) 2-38 m/z = 746.88 (C51H30N4OS =746.21) 2-39 m/z = 746.88 (C51H30N4OS =746.21) 2-40 m/z = 746.88 (C51H30N4OS =746.21) 2-41 m/z= 670.78 (C45H26N4OS=670.18) 2-42 m/z= 670.78 (C45H26N4OS=670.18) 2-43 m/z= 670.78 (C45H26N4OS=670.18) 2-44 m/z= 670.78 (C45H26N4OS=670.18) 2-45 m/z= 670.78 (C45H26N4OS=670.18) 2-46 m/z= 670.78 (C45H26N4OS=670.18) 2-47 m/z= 670.78 (C45H26N4OS=670.18) 2-48 m/z = 675.81 (C45H21D5N4OS =675.21) 2-49 m/z = 675.81 (C45H21D5N4OS =675.21) 2-50 m/z= 670.78 (C45H26N4OS=670.18) 2-51 m/z= 670.78 (C45H26N4OS=670.18) 2-52 m/z= 670.78 (C45H26N4OS=670.18) 2-53 m/z= 670.78 (C45H26N4OS=670.18) 2-54 m/z= 670.78 (C45H26N4OS=670.18) 2-55 m/z= 670.78 (C45H26N4OS=670.18) 2-56 m/z = 675.81 (C45H21D5N4OS =675.21) 2-57 m/z = 746.88 (C51H30N4OS =746.21) 2-58 m/z = 746.88 (C51H30N4OS =746.21) 2-59 m/z = 680.84 (C45H16D10N4OS =680.25) 2-60 m/z = 686.88 (C45H10D16N4OS =686.18) 2-61 m/z = 746.88 (C51H30N4OS =746.21) 2-62 m/z = 746.88 (C51H30N4OS =746.21) 2-63 m/z = 746.88 (C51H30N4OS =746.21) 2-64 m/z = 746.88 (C51H30N4OS =746.21) 2-65 m/z = 746.88 (C51H30N4OS =746.21) 2-66 m/z = 746.88 (C51H30N4OS =746.21) 2-67 m/z = 746.88 (C51H30N4OS =746.21) 2-68 m/z = 746.88 (C51H30N4OS =746.21) 2-69 m/z = 746.88 (C51H30N4OS =746.21) 2-70 m/z = 746.88 (C51H30N4OS =746.21) 2-71 m/z = 746.88 (C51H30N4OS =746.21) 2-72 m/z = 746.88 (C51H30N4OS =746.21) 2-73 m/z = 746.88 (C51H30N4OS =746.21) 2-74 m/z = 746.88 (C51H30N4OS =746.21) 2-75 m/z = 746.88 (C51H30N4OS =746.21) 2-76 m/z = 746.88 (C51H30N4OS =746.21) 2-77 m/z = 746.88 (C51H30N4OS =746.21) 2-78 m/z = 746.88 (C51H30N4OS =746.21) 2-79 m/z = 746.88 (C51H30N4OS =746.21) 2-80 m/z = 746.88 (C51H30N4OS =746.21) 2-81 m/z= 670.78 (C45H26N4OS=670.18) 2-82 m/z= 670.78 (C45H26N4OS=670.18) 2-83 m/z= 670.78 (C45H26N4OS=670.18) 2-84 m/z= 670.78 (C45H26N4OS=670.18) 2-85 m/z= 670.78 (C45H26N4OS=670.18) 2-86 m/z= 670.78 (C45H26N4OS=670.18) 2-87 m/z= 670.78 (C45H26N4OS=670.18) 2-88 m/z= 675.81 (C45H21D5N4OS=675.21) 2-89 m/z= 675.81 (C45H21D5N4OS=675.21) 2-90 m/z= 670.78 (C45H26N4OS=670.18) 2-91 m/z= 670.78 (C45H26N4OS=670.18) 2-92 m/z= 670.78 (C45H26N4OS=670.18) 2-93 m/z= 670.78 (C45H26N4OS=670.18) 2-94 m/z= 670.78 (C45H26N4OS=670.18) 2-95 m/z= 670.78 (C45H26N4OS=670.18) 2-96 m/z= 675.81 (C45H21D5N4OS=675.21) 2-97 m/z= 746.88 (C51H30N4OS=746.21) 2-98 m/z= 746.88 (C51H30N4OS=746.21) 2-99 m/z = 680.84 (C45H16D10N4OS =680.25) 2-100 m/z = 686.88 (C45H10D16N4OS =686.18) 2-101 m/z = 746.88 (C51H30N4OS =746.21) 2-102 m/z = 746.88 (C51H30N4OS =746.21) 2-103 m/z = 746.88 (C51H30N4OS =746.21) 2-104 m/z = 746.88 (C51H30N4OS =746.21) 2-105 m/z = 746.88 (C51H30N4OS =746.21) 2-106 m/z = 746.88 (C51H30N4OS =746.21) 2-107 m/z = 746.88 (C51H30N4OS =746.21) 2-108 m/z = 746.88 (C51H30N4OS =746.21) 2-109 m/z = 746.88 (C51H30N4OS =746.21) 2-110 m/z = 746.88 (C51H30N4OS =746.21) 2-111 m/z = 746.88 (C51H30N4OS =746.21) 2-112 m/z = 746.88 (C51H30N4OS =746.21) 2-113 m/z = 746.88 (C51H30N4OS =746.21) 2-114 m/z = 746.88 (C51H30N4OS =746.21) 2-115 m/z = 746.88 (C51H30N4OS =746.21) 2-116 m/z = 746.88 (C51H30N4OS =746.21) 2-117 m/z = 746.88 (C51H30N4OS =746.21) 2-118 m/z = 746.88 (C51H30N4OS =746.21) 2-119 m/z = 746.88 (C51H30N4OS =746.21) 2-120 m/z = 746.88 (C51H30N4OS =746.21) 2-121 m/z= 670.78 (C45H26N4OS=670.18) 2-122 m/z= 670.78 (C45H26N4OS=670.18) 2-123 m/z= 670.78 (C45H26N4OS=670.18) 2-124 m/z= 670.78 (C45H26N4OS=670.18) 2-125 m/z= 670.78 (C45H26N4OS=670.18) 2-126 m/z= 670.78 (C45H26N4OS=670.18) 2-127 m/z= 670.78 (C45H26N4OS=670.18) 2-128 m/z= 675.81 (C45H21D5N4OS=675.21) 2-129 m/z= 675.81 (C45H21D5N4OS=675.21) 2-130 m/z= 670.78 (C45H26N4OS=670.18) 2-131 m/z= 670.78 (C45H26N4OS=670.18) 2-132 m/z= 670.78 (C45H26N4OS=670.18) 2-133 m/z= 670.78 (C45H26N4OS=670.18) 2-134 m/z= 670.78 (C45H26N4OS=670.18) 2-135 m/z= 670.78 (C45H26N4OS=670.18) 2-136 m/z= 675.81 (C45H21D5N4OS=675.21) 2-137 m/z = 746.88 (C51H30N4OS =746.21) 2-138 m/z = 746.88 (C51H30N4OS =746.21 2-139 m/z = 680.84 (C45H16D10N4OS =680.25) 2-140 m/z = 686.88 (C45H10D16N4OS =686.18) 2-141 m/z = 746.88 (C51H30N4OS =746.21) 2-142 m/z = 746.88 (C51H30N4OS =746.21) 2-143 m/z = 746.88 (C51H30N4OS =746.21) 2-144 m/z = 746.88 (C51H30N4OS =746.21) 2-145 m/z = 746.88 (C51H30N4OS =746.21) 2-146 m/z = 746.88 (C51H30N4OS =746.21) 2-147 m/z = 746.88 (C51H30N4OS =746.21) 2-148 m/z = 746.88 (C51H30N4OS =746.21) 2-149 m/z = 746.88 (C51H30N4OS =746.21) 2-150 m/z = 746.88 (C51H30N4OS =746.21) 2-151 m/z = 746.88 (C51H30N4OS =746.21) 2-152 m/z = 746.88 (C51H30N4OS =746.21) 2-153 m/z = 746.88 (C51H30N4OS =746.21) 2-154 m/z = 746.88 (C51H30N4OS =746.21) 2-155 m/z = 746.88 (C51H30N4OS =746.21) 2-156 m/z = 746.88 (C51H30N4OS =746.21) 2-157 m/z = 746.88 (C51H30N4OS =746.21) 2-158 m/z = 746.88 (C51H30N4OS =746.21) 2-159 m/z = 746.88 (C51H30N4OS =746.21) 2-160 m/z = 746.88 (C51H30N4OS =746.21) 2-161 m/z = 686.84 (C45H26N4S2 =686.16) 2-162 m/z = 686.84 (C45H26N4S2 =686.16) 2-163 m/z = 686.84 (C45H26N4S2 =686.16) 2-164 m/z = 686.84 (C45H26N4S2 =686.16) 2-165 m/z = 762.94 (C51H30N4S2 =762.19) 2-166 m/z = 762.94 (C51H30N4S2 =762.19) 2-167 m/z = 762.94 (C51H30N4S2 =762.19) 2-168 m/z = 762.94 (C51H30N4S2 =762.19) 2-169 m/z = 762.94 (C51H30N4S2 =762.19) 2-170 m/z = 762.94 (C51H30N4S2 =762.19) 2-171 m/z = 762.94 (C51H30N4S2 =762.19) 2-172 m/z = 762.94 (C51H30N4S2 =762.19) 2-173 m/z = 686.84 (C45H26N4S2 =686.16) 2-174 m/z = 686.84 (C45H26N4S2 =686.16) 2-175 m/z = 762.94 (C51H30N4S2 =762.19) 2-176 m/z = 762.94 (C51H30N4S2 =762.19) 2-177 m/z = 762.94 (C51H30N4S2 =762.19) 2-178 m/z = 762.94 (C51H30N4S2 =762.19) 2-179 m/z = 762.94 (C51H30N4S2 =762.19) 2-180 m/z = 762.94 (C51H30N4S2 =762.19) 2-181 m/z = 762.94 (C51H30N4S2 =762.19) 2-182 m/z = 762.94 (C51H30N4S2 =762.19) 2-183 m/z = 762.94 (C51H30N4S2 =762.19) 2-184 m/z = 762.94 (C51H30N4S2 =762.19) 2-185 m/z = 686.84 (C45H26N4S2 =686.16) 2-186 m/z = 686.84 (C45H26N4S2 =686.16) 2-187 m/z = 686.84 (C45H26N4S2 =686.16) 2-188 m/z = 691.88 (C45H21D5N4S2 =691.19) 2-189 m/z = 756.94 (C51H20D10N4OS2 =756.28) 2-190 m/z = 761.97 (C51H15D15N4OS2 =761.4) 2-191 m/z = 751.91 (C51H25D5N4OS2 =751.25) 2-192 m/z = 756.94 (C51H20D10N4OS2 =756.28) 2-193 m/z = 756.94 (C51H20D10N4OS2 =756.28) 2-194 m/z = 776.05 (C51D30N4OS2 =775.40) 2-195 m/z = 756.94 (C51H20D10N4OS2 =756.28) 2-196 m/z = 756.94 (C51H20D10N4OS2 =756.28) 2-197 m/z= 696.94 (C45D26N4OS2 =696.35) 2-198 m/z = 686.88 (C45H10D16N4S2 =686.28) 2-199 m/z = 680.84 (C45H16D10N4S2 =680.25) 2-200 m/z = 696.94 (C45D26N4S2 =696.35) 2-201 m/z = 696.86 (C48H32N4S2 =696.23) 2-202 m/z = 696.86 (C48H32N4S2 =696.23) 2-203 m/z = 696.86 (C48H32N4S2 =696.23) 2-204 m/z = 696.86 (C48H32N4S2 =696.23) 2-205 m/z = 772.96 (C48H32N4S2 =772.27) 2-206 m/z = 772.96 (C48H32N4S2 =772.27) 2-207 m/z = 772.96 (C48H32N4S2 =772.27) 2-208 m/z = 772.96 (C48H32N4S2 =772.27) 2-209 m/z = 772.96 (C48H32N4S2 =772.27) 2-210 m/z = 772.96 (C48H32N4S2 =772.27) 2-211 m/z = 772.96 (C48H32N4S2 =772.27) 2-212 m/z = 772.96 (C48H32N4S2 =772.27) 2-213 m/z = 696.86 (C48H32N4S2 =696.23) 2-214 m/z = 696.86 (C48H32N4S2 =696.23) 2-215 m/z = 696.86 (C48H32N4S2 =696.23) 2-216 m/z = 696.86 (C48H32N4S2 =696.23) 2-217 m/z = 772.96 (C48H32N4S2 =772.27) 2-218 m/z = 772.96 (C48H32N4S2 =772.27) 2-219 m/z = 772.96 (C48H32N4S2 =772.27) 2-220 m/z = 772.96 (C48H32N4S2 =772.27) 3-1 m/z = 654.71 (C45H26N4O2 =654.21) 3-2 m/z = 654.71 (C45H26N4O2 =654.21) 3-3 m/z = 654.71 (C45H26N4O2 =654.21) 3-4 m/z = 654.71 (C45H26N4O2 =654.21) 3-5 m/z = 653.73 (C46H27N3O2 =653.21) 3-6 m/z = 653.73 (C46H27N3O2 =653.21) 3-7 m/z = 653.73 (C46H27N3O2 =653.21) 3-8 m/z = 675.81 (C45H21D5N4O2 =675.21) 3-9 m/z = 675.81 (C45H21D5N4O2 =675.21) 3-10 m/z = 654.71 (C45H26N4O2 =654.21) 3-11 m/z = 654.71 (C45H26N4O2 =654.21) 3-12 m/z = 654.71 (C45H26N4O2 =654.21) 3-13 m/z = 654.71 (C45H26N4O2 =654.21) 3-14 m/z = 654.71 (C45H26N4O2 =654.21) 3-15 m/z = 654.71 (C45H26N4O2 =654.21) 3-16 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-17 m/z = 730.81 (C51H30N4O2 =730.24) 3-18 m/z = 730.81 (C51H30N4O2 =730.24) 3-19 m/z = 664.78 (C45H16D10N4O2 =664.27) 3-20 m/z = 670.81 (C45H10D16N4O2 =670.31) 3-21 m/z = 730.81 (C51H30N4O2 =730.24) 3-22 m/z = 730.81 (C51H30N4O2 =730.24) 3-23 m/z = 730.81 (C51H30N4O2 =730.24) 3-24 m/z = 730.81 (C51H30N4O2 =730.24) 3-25 m/z = 730.81 (C51H30N4O2 =730.24) 3-26 m/z = 730.81 (C51H30N4O2 =730.24) 3-27 m/z = 730.81 (C51H30N4O2 =730.24) 3-28 m/z = 730.81 (C51H30N4O2 =730.24) 3-29 m/z = 730.81 (C51H30N4O2 =730.24) 3-30 m/z = 730.81 (C51H30N4O2 =730.24) 3-31 m/z = 730.81 (C51H30N4O2 =730.24) 3-32 m/z = 730.81 (C51H30N4O2 =730.24) 3-33 m/z = 730.81 (C51H30N4O2 =730.24) 3-34 m/z = 730.81 (C51H30N4O2 =730.24) 3-35 m/z = 730.81 (C51H30N4O2 =730.24) 3-36 m/z = 730.81 (C51H30N4O2 =730.24) 3-37 m/z = 730.81 (C51H30N4O2 =730.24) 3-38 m/z = 730.81 (C51H30N4O2 =730.24) 3-39 m/z = 730.81 (C51H30N4O2 =730.24) 3-40 m/z = 730.81 (C51H30N4O2 =730.24) 3-41 m/z = 654.71 (C45H26N4O2 =654.21) 3-42 m/z = 654.71 (C45H26N4O2 =654.21) 3-43 m/z = 654.71 (C45H26N4O2 =654.21) 3-44 m/z = 654.71 (C45H26N4O2 =654.21) 3-45 m/z = 654.71 (C45H26N4O2 =654.21) 3-46 m/z = 654.71 (C45H26N4O2 =654.21) 3-47 m/z = 654.71 (C45H26N4O2 =654.21) 3-48 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-49 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-50 m/z = 654.71 (C45H26N4O2 =654.21) 3-51 m/z = 654.71 (C45H26N4O2 =654.21) 3-52 m/z = 654.71 (C45H26N4O2 =654.21) 3-53 m/z = 654.71 (C45H26N4O2 =654.21) 3-54 m/z = 654.71 (C45H26N4O2 =654.21) 3-55 m/z = 654.71 (C45H26N4O2 =654.21) 3-56 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-57 m/z = 730.81 (C51H30N4O2 =730.24) 3-58 m/z = 730.81 (C51H30N4O2 =730.24) 3-59 m/z = 664.78 (C45H16D10N4O2 =664.27) 3-60 m/z = 670.81 (C45H10D16N4O2 =670.31) 3-61 m/z = 730.81 (C51H3N4O2 =730.24) 3-62 m/z = 730.81 (C51H3N4O2 =730.24) 3-63 m/z = 730.81 (C51H3N4O2 =730.24) 3-64 m/z = 730.81 (C51H3N4O2 =730.24) 3-65 m/z = 730.81 (C51H3N4O2 =730.24) 3-66 m/z = 730.81 (C51H3N4O2 =730.24) 3-67 m/z = 730.81 (C51H3N4O2 =730.24) 3-68 m/z = 730.81 (C51H3N4O2 =730.24) 3-69 m/z = 730.81 (C51H3N4O2 =730.24) 3-70 m/z = 730.81 (C51H3N4O2 =730.24) 3-71 m/z = 730.81 (C51H3N4O2 =730.24) 3-72 m/z = 730.81 (C51H3N4O2 =730.24) 3-73 m/z = 730.81 (C51H3N4O2 =730.24) 3-74 m/z = 730.81 (C51H3N4O2 =730.24) 3-75 m/z = 730.81 (C51H3N4O2 =730.24) 3-76 m/z = 730.81 (C51H3N4O2 =730.24) 3-77 m/z = 730.81 (C51H3N4O2 =730.24) 3-78 m/z = 730.81 (C51H3N4O2 =730.24) 3-79 m/z = 730.81 (C51H3N4O2 =730.24) 3-80 m/z = 730.81 (C51H3N4O2 =730.24) 3-81 m/z = 654.71 (C45H26N4O2 =654.21) 3-82 m/z = 654.71 (C45H26N4O2 =654.21) 3-83 m/z = 654.71 (C45H26N4O2 =654.21) 3-84 m/z = 654.71 (C45H26N4O2 =654.21) 3-85 m/z = 654.71 (C45H26N4O2 =654.21) 3-86 m/z = 654.71 (C45H26N4O2 =654.21) 3-87 m/z = 654.71 (C45H26N4O2 =654.21) 3-88 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-89 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-90 m/z = 654.71 (C45H26N4O2 =654.21) 3-91 m/z = 654.71 (C45H26N4O2 =654.21) 3-92 m/z = 654.71 (C45H26N4O2 =654.21) 3-93 m/z = 654.71 (C45H26N4O2 =654.21) 3-94 m/z = 654.71 (C45H26N4O2 =654.21) 3-95 m/z = 654.71 (C45H26N4O2 =654.21) 3-96 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-97 m/z = 730.81 (C51H3N4O2 =730.24) 3-98 m/z = 730.81 (C51H3N4O2 =730.24) 3-99 m/z = 664.78 (C45H16D10N4O2 =664.27) 3-100 m/z = 670.81 (C45H10D16N4O2 =670.31) 3-101 m/z = 730.81 (C51H3N4O2 =730.24) 3-102 m/z = 730.81 (C51H3N4O2 =730.24) 3-103 m/z = 730.81 (C51H3N4O2 =730.24) 3-104 m/z = 730.81 (C51H3N4O2 =730.24) 3-105 m/z = 730.81 (C51H3N4O2 =730.24) 3-106 m/z = 730.81 (C51H3N4O2 =730.24) 3-107 m/z = 730.81 (C51H3N4O2 =730.24) 3-108 m/z = 730.81 (C51H3N4O2 =730.24) 3-109 m/z = 730.81 (C51H3N4O2 =730.24) 3-110 m/z = 730.81 (C51H3N4O2 =730.24) 3-111 m/z = 730.81 (C51H3N4O2 =730.24) 3-112 m/z = 730.81 (C51H3N4O2 =730.24) 3-113 m/z = 730.81 (C51H3N4O2 =730.24) 3-114 m/z = 730.81 (C51H3N4O2 =730.24) 3-115 m/z = 730.81 (C51H3N4O2 =730.24) 3-116 m/z = 730.81 (C51H3N4O2 =730.24) 3-117 m/z = 730.81 (C51H3N4O2 =730.24) 3-118 m/z = 730.81 (C51H3N4O2 =730.24) 3-119 m/z = 730.81 (C51H3N4O2 =730.24) 3-120 m/z = 730.81 (C51H3N4O2 =730.24) 3-121 m/z = 654.71 (C45H26N4O2 =654.21) 3-122 m/z = 654.71 (C45H26N4O2 =654.21) 3-123 m/z = 654.71 (C45H26N4O2 =654.21) 3-124 m/z = 654.71 (C45H26N4O2 =654.21) 3-125 m/z = 654.71 (C45H26N4O2 =654.21) 3-126 m/z = 654.71 (C45H26N4O2 =654.21) 3-127 m/z = 654.71 (C45H26N4O2 =654.21) 3-128 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-129 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-130 m/z = 654.71 (C45H26N4O2 =654.21) 3-131 m/z = 654.71 (C45H26N4O2 =654.21) 3-132 m/z = 654.71 (C45H26N4O2 =654.21) 3-133 m/z = 654.71 (C45H26N4O2 =654.21) 3-134 m/z = 654.71 (C45H26N4O2 =654.21) 3-135 m/z = 654.71 (C45H26N4O2 =654.21) 3-136 m/z = 659.74 (C45H21D5N4O2 =659.24) 3-137 m/z = 730.81 (C51H3N4O2 =730.24) 3-138 m/z = 730.81 (C51H3N4O2 =730.24) 3-139 m/z = 664.78 (C45H16D10N4O2 =664.27) 3-140 m/z = 670.81 (C45H10D16N4O2 =670.31) 3-141 m/z = 730.81 (C51H3N4O2 =730.24) 3-142 m/z = 730.81 (C51H3N4O2 =730.24) 3-143 m/z = 730.81 (C51H3N4O2 =730.24) 3-144 m/z = 730.81 (C51H3N4O2 =730.24) 3-145 m/z = 730.81 (C51H3N4O2 =730.24) 3-146 m/z = 730.81 (C51H3N4O2 =730.24) 3-147 m/z = 730.81 (C51H3N4O2 =730.24) 3-148 m/z = 730.81 (C51H3N4O2 =730.24) 3-149 m/z = 730.81 (C51H3N4O2 =730.24) 3-150 m/z = 730.81 (C51H3N4O2 =730.24) 3-151 m/z = 730.81 (C51H3N4O2 =730.24) 3-152 m/z = 730.81 (C51H3N4O2 =730.24) 3-153 m/z = 730.81 (C51H3N4O2 =730.24) 3-154 m/z = 730.81 (C51H3N4O2 =730.24) 3-155 m/z = 730.81 (C51H3N4O2 =730.24) 3-156 m/z = 730.81 (C51H3N4O2 =730.24) 3-157 m/z = 730.81 (C51H3N4O2 =730.24) 3-158 m/z = 730.81 (C51H3N4O2 =730.24) 3-159 m/z = 730.81 (C51H3N4O2 =730.24) 3-160 m/z = 730.81 (C51H3N4O2 =730.24) 3-161 m/z = 670.78 (C45H26N4O2 =670.18) 3-162 m/z = 670.78 (C45H26N4O2 =670.18) 3-163 m/z = 670.78 (C45H26N4O2 =670.18) 3-164 m/z = 670.78 (C45H26N4O2 =670.18) 3-165 m/z = 746.88 (C45H26N4O2 =746.21) 3-166 m/z = 746.88 (C45H26N4O2 =746.21) 3-167 m/z = 746.88 (C45H26N4O2 =746.21) 3-168 m/z = 746.88 (C45H26N4O2 =746.21) 3-169 m/z = 746.88 (C45H26N4O2 =746.21) 3-170 m/z = 746.88 (C45H26N4O2 =746.21) 3-171 m/z = 746.88 (C45H26N4O2 =746.21) 3-172 m/z = 746.88 (C45H26N4O2 =746.21) 3-173 m/z = 670.78 (C45H26N4O2 =670.18) 3-174 m/z = 670.78 (C45H26N4O2 =670.18) 3-175 m/z = 670.78 (C45H26N4O2 =670.18) 3-176 m/z = 670.78 (C45H26N4O2 =670.18) 3-177 m/z = 670.78 (C45H26N4O2 =670.18) 3-178 m/z = 670.78 (C45H26N4O2 =670.18) 3-179 m/z = 670.78 (C45H26N4O2 =670.18) 3-180 m/z = 670.78 (C45H26N4O2 =670.18) 3-181 m/z = 746.88 (C45H26N4O2 =746.21) 3-182 m/z = 746.88 (C45H26N4O2 =746.21) 3-183 m/z = 746.88 (C45H26N4O2 =746.21) 3-184 m/z = 746.88 (C45H26N4O2 =746.21) 3-185 m/z = 670.78 (C45H26N4O2 =670.18) 3-186 m/z = 670.78 (C45H26N4O2 =670.18) 3-187 m/z = 670.78 (C45H26N4O2 =670.18) 3-188 m/z = 675.81 (C45H21D5N4O2 =675.21) 3-189 m/z = 740.87 (C51H21D10N4O2 =740.30) 3-190 m/z = 745.90 (C51H15D15N4O2 =745.33) 3-191 m/z = 735.84 (C51H25D5N4O2 =735.27) 3-192 m/z = 740.87 (C51H21D10N4O2 =740.30) 3-193 m/z = 740.87 (C51H21D10N4O2 =740.30) 3-194 m/z = 760.99 (C51D30N4O2 =760.43) 3-195 m/z = 740.87 (C51H21D10N4O2 =740.30) 3-196 m/z = 740.87 (C51H21D10N4O2 =740.30) 3-197 m/z = 680.87 (C45D26N4O2 =680.37) 3-198 m/z = 670.78 (C45H26N4O2 =670.18) 3-199 m/z = 664.78 (C45H16D10N4O2 =664.27) 3-200 m/z = 680.87 (C45D26N4O2 =680.37) 3-201 m/z = 680.79 (C48H32N4O =680.26) 3-202 m/z = 680.79 (C48H32N4O =680.26) 3-203 m/z = 680.79 (C48H32N4O =680.26) 3-204 m/z = 680.79 (C48H32N4O =680.26) 3-205 m/z = 756.89 (C54H36N4O =756.29) 3-206 m/z = 756.89 (C54H36N4O =756.29) 3-207 m/z = 756.89 (C54H36N4O =756.29) 3-208 m/z = 756.89 (C54H36N4O =756.29) 3-209 m/z = 756.89 (C54H36N4O =756.29) 3-210 m/z = 756.89 (C54H36N4O =756.29) 3-211 m/z = 756.89 (C54H36N4O =756.29) 3-212 m/z = 756.89 (C54H36N4O =756.29) 3-213 m/z = 680.79 (C48H32N4O =680.26) 3-214 m/z = 680.79 (C48H32N4O =680.26) 3-215 m/z = 680.79 (C48H32N4O =680.26) 3-216 m/z = 680.79 (C48H32N4O =680.26) 3-217 m/z = 756.89 (C54H36N4O =756.29) 3-218 m/z = 756.89 (C54H36N4O =756.29) 3-219 m/z = 756.89 (C54H36N4O =756.29) 3-220 m/z = 756.89 (C54H36N4O =756.29) 4-1 m/z= 756.89 (C54H36N4O= 756.29) 4-2 m/z= 756.89 (C54H36N4O= 756.29) 4-3 m/z= 756.89 (C54H36N4O= 756.29) 4-4 m/z= 756.89 (C54H36N4O= 756.29) 4-5 m/z= 756.89 (C54H36N4O= 756.29) 4-6 m/z= 756.89 (C54H36N4O= 756.29) 4-7 m/z= 756.89 (C54H36N4O= 756.29) 4-8 m/z= 761.92 (C54H31D5N4O= 761.32) 4-9 m/z= 832.99 (C60H40N4O= 832.32) 4-10 m/z= 832.99 (C60H40N4O= 832.32) 4-11 m/z= 832.99 (C60H40N4O= 832.32) 4-12 m/z= 832.99 (C60H40N4O= 832.32) 4-13 m/z= 832.99 (C60H40N4O= 832.32) 4-14 m/z= 832.99 (C60H40N4O= 832.32) 4-15 m/z= 832.99 (C60H40N4O= 832.32) 4-16 m/z= 832.99 (C60H40N4O= 832.32) 4-17 m/z= 756.89 (C54H36N4O= 756.29) 4-18 m/z= 756.89 (C54H36N4O= 756.29) 4-19 m/z= 756.89 (C54H36N4O= 756.29) 4-20 m/z= 756.89 (C54H36N4O= 756.29) 4-21 m/z= 756.89 (C54H36N4O= 756.29) 4-22 m/z= 756.89 (C54H36N4O= 756.29) 4-23 m/z= 756.89 (C54H36N4O= 756.29) 4-24 m/z= 761.92 (C54H31D5N4O= 761.32) 4-25 m/z= 832.99 (C60H40N4O= 832.32) 4-26 m/z= 832.99 (C60H40N4O= 832.32) 4-27 m/z= 832.99 (C60H40N4O= 832.32) 4-28 m/z= 832.99 (C60H40N4O= 832.32) 4-29 m/z= 832.99 (C60H40N4O= 832.32) 4-30 m/z= 832.99 (C60H40N4O= 832.32) 4-31 m/z= 832.99 (C60H40N4O= 832.32) 4-32 m/z= 832.99 (C60H40N4O= 832.32) 4-33 m/z= 746.88 (C51H30N4O= 746.21) 4-34 m/z= 746.88 (C51H30N4O= 746.21) 4-35 m/z= 746.88 (C51H30N4O= 746.21) 4-36 m/z= 746.88 (C51H30N4O= 746.21) 4-37 m/z= 746.88 (C51H30N4O= 746.21) 4-38 m/z= 746.88 (C51H30N4O= 746.21) 4-39 m/z= 746.88 (C51H30N4O= 746.21) 4-40 m/z= 751.91 (C51H25D5N4O= 751.25) 4-41 m/z= 822.97 (C57H34N4OS= 822.25) 4-42 m/z= 822.97 (C57H34N4OS= 822.25) 4-43 m/z= 822.97 (C57H34N4OS= 822.25) 4-44 m/z= 822.97 (C57H34N4OS= 822.25) 4-45 m/z= 822.97 (C57H34N4OS= 822.25) 4-46 m/z= 822.97 (C57H34N4OS= 822.25) 4-47 m/z= 822.97 (C57H34N4OS= 822.25) 4-48 m/z= 822.97 (C57H34N4OS= 822.25) 4-49 m/z = 751.91 (C51H25D5N4OS = 751.25) 4-50 m/z= 746.88 (C51H30N4O= 746.21) 4-51 m/z= 746.88 (C51H30N4O= 746.21) 4-52 m/z= 746.88 (C51H30N4O= 746.21) 4-53 m/z= 746.88 (C51H30N4O= 746.21) 4-54 m/z= 746.88 (C51H30N4O= 746.21) 4-55 m/z= 746.88 (C51H30N4O= 746.21) 4-56 m/z = 751.91 (C51H25D5N4OS = 751.25) 4-57 m/z= 822.97 (C57H34N4OS= 822.25) 4-58 m/z= 822.97 (C57H34N4OS= 822.25) 4-59 m/z= 822.97 (C57H34N4OS= 822.25) 4-60 m/z= 822.97 (C57H34N4OS= 822.25) 4-61 m/z= 822.97 (C57H34N4OS= 822.25) 4-62 m/z= 822.97 (C57H34N4OS= 822.25) 4-63 m/z= 822.97 (C57H34N4OS= 822.25) 4-64 m/z= 822.97 (C57H34N4OS= 822.25) 4-65 m/z= 746.88 (C51H30N4O= 746.21) 4-66 m/z= 746.88 (C51H30N4O= 746.21) 4-67 m/z= 746.88 (C51H30N4O= 746.21) 4-68 m/z = 751.91 (C51H25D5N4OS = 751.25) 4-69 m/z = 751.91 (C51H25D5N4OS = 751.25) 4-70 m/z= 746.88 (C51H30N4O= 746.21) 4-71 m/z= 746.88 (C51H30N4O= 746.21) 4-72 m/z= 746.88 (C51H30N4O= 746.21) 4-73 m/z= 822.97 (C57H34N4OS= 822.25) 4-74 m/z= 822.97 (C57H34N4OS= 822.25) 4-75 m/z= 822.97 (C57H34N4OS= 822.25) 4-76 m/z= 822.97 (C57H34N4OS= 822.25) 4-77 m/z= 822.97 (C57H34N4OS= 822.25) 4-78 m/z= 822.97 (C57H34N4OS= 822.25) 4-79 m/z= 822.97 (C57H34N4OS= 822.25) 4-80 m/z= 822.97 (C57H34N4OS= 822.25) 4-81 m/z= 746.88 (C51H30N4O= 746.21) 4-82 m/z= 746.88 (C51H30N4O= 746.21) 4-83 m/z= 746.88 (C51H30N4O= 746.21) 4-84 m/z= 746.88 (C51H30N4O= 746.21) 4-85 m/z= 746.88 (C51H30N4O= 746.21) 4-86 m/z= 746.88 (C51H30N4O= 746.21) 4-87 m/z= 746.88 (C51H30N4O= 746.21) 4-88 m/z= 746.88 (C51H30N4O= 746.21) 4-89 m/z= 822.97 (C57H34N4OS= 822.25) 4-90 m/z= 822.97 (C57H34N4OS= 822.25) 4-91 m/z= 822.97 (C57H34N4OS= 822.25) 4-92 m/z= 822.97 (C57H34N4OS= 822.25) 4-93 m/z= 822.97 (C57H34N4OS= 822.25) 4-94 m/z= 822.97 (C57H34N4OS= 822.25) 4-95 m/z= 822.97 (C57H34N4OS= 822.25) 4-96 m/z= 822.97 (C57H34N4OS= 822.25) 4-97 m/z= 735.84 (C51H25D5N4O= 735.27) 4-98 m/z= 730.81 (C51H30N4O= 730.24) 4-99 m/z= 730.81 (C51H30N4O= 730.24) 4-100 m/z= 730.81 (C51H30N4O= 730.24) 4-101 m/z= 730.81 (C51H30N4O= 730.24) 4-102 m/z= 730.81 (C51H30N4O= 730.24) 4-103 m/z= 730.81 (C51H30N4O= 730.24) 4-104 m/z= 735.84 (C51H25D5N4O= 735.27) 4-105 m/z= 730.81 (C51H30N4O= 730.24) 4-106 m/z= 730.81 (C51H30N4O= 730.24) 4-107 m/z= 730.81 (C51H30N4O= 730.24) 4-108 m/z= 730.81 (C51H30N4O= 730.24) 4-109 m/z= 730.81 (C51H30N4O= 730.24) 4-110 m/z= 730.81 (C51H30N4O= 730.24) 4-111 m/z= 730.81 (C51H30N4O= 730.24) 4-112 m/z= 735.84 (C51H25D5N4O= 735.27) 4-113 m/z= 806.91 (C57H34N4O2= 806.27) 4-114 m/z= 806.91 (C57H34N4O2= 806.27) 4-115 m/z= 806.91 (C57H34N4O2= 806.27) 4-116 m/z= 806.91 (C57H34N4O2= 806.27) 4-117 m/z= 806.91 (C57H34N4O2= 806.27) 4-118 m/z= 806.91 (C57H34N4O2= 806.27) 4-119 m/z= 806.91 (C57H34N4O2= 806.27) 4-120 m/z= 806.91 (C57H34N4O2= 806.27) 4-121 m/z= 730.81 (C51H30N4O= 730.24) 4-122 m/z= 730.81 (C51H30N4O= 730.24) 4-123 m/z= 730.81 (C51H30N4O= 730.24) 4-124 m/z= 730.81 (C51H30N4O= 730.24) 4-125 m/z= 730.81 (C51H30N4O= 730.24) 4-126 m/z= 730.81 (C51H30N4O= 730.24) 4-127 m/z= 730.81 (C51H30N4O= 730.24) 4-128 m/z= 735.84 (C51H25D5N4O= 735.27) 4-129 m/z= 806.91 (C57H34N4O2= 806.27) 4-130 m/z= 806.91 (C57H34N4O2= 806.27) 4-131 m/z= 806.91 (C57H34N4O2= 806.27) 4-132 m/z= 806.91 (C57H34N4O2= 806.27) 4-133 m/z= 806.91 (C57H34N4O2= 806.27) 4-134 m/z= 806.91 (C57H34N4O2= 806.27) 4-135 m/z= 806.91 (C57H34N4O2= 806.27) 4-136 m/z= 806.91 (C57H34N4O2= 806.27) 4-137 m/z= 730.81 (C51H30N4O= 730.24) 4-138 m/z= 730.81 (C51H30N4O= 730.24) 4-139 m/z= 730.81 (C51H30N4O= 730.24) 4-140 m/z= 730.81 (C51H30N4O= 730.24) 4-141 m/z= 730.81 (C51H30N4O= 730.24) 4-142 m/z= 730.81 (C51H30N4O= 730.24) 4-143 m/z= 730.81 (C51H30N4O= 730.24) 4-144 m/z= 735.84 (C51H25D5N4O= 735.27) 4-145 m/z=679.81 (C49H33N3O=679.26) 4-146 m/z=679.81 (C49H33N3O=679.26) 4-147 m/z=679.81 (C49H33N3O=679.26) 4-148 m/z=679.81 (C49H33N3O=679.26) 4-149 m/z=678.82 (C50H34N2O=678.27) 4-150 m/z=678.82 (C50H34N2O=678.27) 4-151 m/z=678.82 (C50H34N2O=678.27) 4-152 m/z=648.84 (C49H28D5N3O=648.29) 4-153 m/z=674.82 (C46H22D5N3OS=674.22) 4-154 m/z=669.79 (C46H27N3OS=669.19) 4-155 m/z=669.79 (C46H27N3OS=669.19) 4-156 m/z=653.73 (C46H27N3O2=653.21) 4-157 m/z=730.85 (C52H34N4O=730.27) 4-158 m/z=730.85 (C52H34N4O=730.27) 4-159 m/z=756.89(C54H36N4)==756.29) 4-160 m/z=760.91 (C54H32D4N4O=760.31) 4-161 m/z=796.93 (C55H32N4OS=796.23) 4-162 m/z=909.08 (C66H44N4O=908.35) 4-163 m/z=740.91 (C52H24D10N4O=740.34) 4-166 m/z=658.89 (C46H11D16N3OS=658.29) A-1 m/z= 484.19 (C36H24N2=484.60) A-2 m/z= 560.23 (C42H28N2=560.70) A-3 m/z= 560.23 (C42H28N2=560.70) A-4 m/z= 560.23 (C42H28N2=560.70) A-5 m/z= 636.26 (C48H32N2=636.80) A-6 m/z= 636.26 (C48H32N2=636.80) A-7 m/z= 636.26 (C48H32N2=636.80) A-8 m/z= 534.21 (C40H26N2=534.66) A-9 m/z= 534.21 (C40H26N2=534.66) A-10 m/z= 600.26 (C45H32N2=600.76) A-11 m/z= 600.26 (C45H32N2=600.76) A-12 m/z= 724.29 (C55H36N2=724.91) A-13 m/z= 724.29 (C55H36N2=724.91) A-14 m/z= 722.27 (C55H34N2=722.89) A-15 m/z= 722.27 (C55H34N2=722.89) A-16 m/z= 634.24 (C48H30N2=634.78) A-17 m/z = 509.19 (C37H23N3=509.61) A-18 m/z = 742.28 (C54H38N2Si=743.00) A-19 m/z= 636.26 (C48H32N2=636.80) A-20 m/z= 636.26 (C48H32N2=636.80) A-21 m/z= 636.26 (C48H32N2=636.80) A-22 m/z= 712.29 (C54H36N2=712.90) A-23 m/z= 712.29 (C54H36N2=712.90) A-24 m/z= 712.29 (C54H36N2=712.90) A-25 m/z= 610.24 (C46H30N2=610.76) A-26 m/z= 610.24 (C46H30N2=610.76) A-27 m/z= 676.29 (C51H36N2=676.86) A-28 m/z= 710.27 (C54H34N2=710.88) A-29 m/z= 585.22 (C43H27N3=585.71) A-30 m/z= 818.31 (C60H42N2Si=819.10) A-31 m/z= 636.26 (C48H32N2=636.80) A-32 m/z= 636.26 (C48H32N2=636.80) A-33 m/z= 712.29 (C54H36N2=712.90) A-34 m/z= 712.29 (C54H36N2=712.90) A-35 m/z= 712.29 (C54H36N2=712.90) A-36 m/z= 610.24 (C46H30N2=610.76) A-37 m/z= 610.24 (C46H30N2=610.76) A-38 m/z= 676.29 (C51H36N2=676.86) A-39 m/z= 710.27 (C54H34N2=710.88) A-40 m/z= 585.22 (C43H27N3=585.71) A-41 m/z= 818.31 (C60H42N2Si=819.10) A-42 m/z= 636.26 (C48H32N2=636.80) A-43 m/z= 712.29 (C54H36N2=712.90) A-44 m/z= 712.29 (C54H36N2=712.90) A-45 m/z= 712.29 (C54H36N2=712.90) A-46 m/z= 610.24 (C46H30N2=610.76) A-47 m/z= 610.24 (C46H30N2=610.76) A-48 m/z= 676.29 (C51H36N2=676.86) A-49 m/z= 710.27 (C54H34N2=710.88) A-50 m/z= 585.22 (C43H27N3=585.71) A-51 m/z= 818.31 (C60H42N2Si=819.10) A-52 m/z= 788.32 (C60H40N2=788.99) A-53 m/z= 788.32 (C60H40N2=788.99) A-54 m/z= 788.32 (C60H40N2=788.99) A-55 m/z= 686.27 (C52H34N2=686.86) A-56 m/z= 686.27 (C52H34N2=686.86) A-57 m/z= 752.32 (C57H40N2=752.96) A-58 m/z= 786.30 (C60H38N2=786.98) A-59 m/z= 661.25 (C49H31N3=661.81) A-60 m/z= 894.34 (C66H46N2Si=895.19) A-61 m/z= 788.32 (C60H40N2=788.99) A-62 m/z= 788.32 (C60H40N2=788.99) A-63 m/z= 686.27 (C52H34N2=686.86) 2-64 m/z= 686.27 (C52H34N2=686.86) A-65 m/z= 752.32 (C57H40N2=752.96) A-66 m/z= 786.30 (C60H38N2=786.98) A-67 m/z= 661.25 (C49H31N3=661.81) A-68 m/z= 894.34 (C66H46N2Si=895.19) A-69 m/z= 788.32 (C60H40N2=788.99) A-70 m/z= 686.27 (C52H34N2=686.86) A-71 m/z= 686.27 (C52H34N2=686.86) A-72 m/z= 752.32 (C57H40N2=752.96) A-73 m/z= 786.30 (C60H38N2=786.98) A-74 m/z= 661.25 (C49H31N3=661.81) A-75 m/z= 894.34 (C66H46N2Si=895.19) A-76 m/z= 584.23 (C44H28N2=584.72) A-77 m/z= 584.23 (C44H28N2=584.72) A-78 m/z= 650.27 (C49H34N2=650.83) A-79 m/z= 684.26 (C52H32N2=684.84) A-80 m/z= 559.20 (C41H25N3=559.67) A-81 m/z = 792.30 (C58H40N2Si=793.06) A-82 m/z= 584.23 (C44H28N2=584.72) A-83 m/z= 650.27 (C49H34N2=650.83) A-84 m/z= 684.26 (C52H32N2=684.84) A-85 m/z= 559.20 (C41H25N3=559.67) A-86 m/z = 792.30 (C58H40N2Si=793.06) A-87 m/z= 716.32 (C54H40N2=716.93) A-88 m/z= 750.30 (C57H38N2=750.94) A-89 m/z= 625.25 (C46H31N3=625.77) A-90 m/z= 858.34 (C63H46N2Si=859.16) A-91 m/z= 784.29 (C60H36N2=784.96) A-92 m/z= 659.24 (C49H29N3=659.79) A-93 m/z= 892.33 (C66H44N2Si=893.18) A-94 m/z= 534.18 (C38H22N4=534.62) A-95 m/z = 767.28 (C55H37N3Si=768.01) A-96 m/z= 1000.37 (C72H52N2Si2=1001.39) A-97 m/z=712.88 (C54H36N2=712.29) A-98 m/z=508.74 (C30D24N2=508.34) A-99 m/z=588.86 (C42D28N2=588.40) A-100 m/z=588.86 (C42D28N2=588.40) A-101 m/z=749.10 (C54D36N2=748.51) A-102 m/z=668.98 (C48D32N2=668.46) A-103 m/z=668.98 (C48D32N2=668.46) A-104 m/z=668.98 (C48D32N2=668.46) A-105 m/z=749.10 (C54D36N2=748.51) A-106 m/z=749.10 (C54D36N2=748.51) A-107 m/z=749.10 (C54D36N2=748.51) A-108 m/z=749.10 (C54D36N2=748.51)

<Experimental Example 1>

1) Fabrication of organic light emitting device

A glass substrate coated with ITO thin film to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, and after drying, UVO treatment was performed for 5 minutes using UV in a UV cleaner.

Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation equipment for organic deposition.

The hole injection layer 2-TNATA (4,4', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) and the hole transport layer NPB (N, N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. The light emitting layer uses the compounds listed in Table 6 below as a host and Ir(ppy) ₃ (tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, and Ir(ppy) ₃ is used as a host based on the weight of the entire light emitting layer. It was doped with 7 wt% and deposited at 400 Å. Thereafter, 60 Å of bathocuproine (hereinafter referred to as BCP) was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transport layer. 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 on the electron injection layer to a thickness of 1200 Å to form a cathode, thereby forming an organic A light emitting device was manufactured.

Specifically, Compounds A to D used in Comparative Examples 1 to 4 were as follows.

<Comparative Example Compound>

2) Evaluation of organic light emitting devices

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with McScience's M7000, and with the measurement result, the standard luminance was 6,000 cd through life measurement equipment (M6000) manufactured by McScience. /m ² , T ₉₀ was measured. Table 6 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured according to the present invention.

compound drive voltage
(V) luminous efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 A 5.72 46.7 (0.273, 0.684) 55 Comparative Example 2 B 5.55 50.2 (0.277, 0.674) 65 Comparative Example 3 C 5.23 59.2 (0.271, 0.686) 43 Comparative Example 4 D 5.42 52.7 (0.273, 0.684) 51 Example 1 1-2 4.01 70.2 (0.277, 0.669) 154 Example 2 1-3 3.62 77.3 (0.281, 0.679) 149 Example 3 1-4 3.66 75.2 (0.280, 0.677) 148 Example 4 1-5 3.98 72.7 (0.279, 0.676) 154 Example 5 1-6 4.64 77.2 (0.272, 0.669) 138 Example 6 1-7 4.32 66.4 (0.271, 0.671) 135 Example 7 1-18 3.88 67.2 (0.275, 0.672) 158 Example 8 1-19 3.74 75.3 (0.279, 0.675) 162 Example 9 1-22 3.84 71.4 (0.280, 0.676) 170 Example 10 1-23 3.72 72.6 (0.278, 0.672) 169 Example 11 1-24 4.53 63.4 (0.283, 0.687) 134 Example 12 1-26 4.32 60.2 (0.286, 0.686) 138 Example 13 1-30 4.42 67.4 (0.274, 0.678) 102 Example 14 1-37 3.99 65.2 (0.279, 0.677) 169 Example 15 1-41 3.88 74.2 (0.278, 0.677) 160 Example 16 1-44 4.02 63.3 (0.276, 0.671) 152 Example 17 1-48 4.46 65.4 (0.284, 0.687) 149 Example 18 1-66 4.51 67.4 (0.281, 0.684) 153 Example 19 1-76 4.21 69.2 (0.283, 0.681) 146 Example 20 1-77 4.11 63.5 (0.279, 0.681) 146 Example 21 1-80 4.08 66.7 (0.280, 0.679) 132 Example 22 1-81 4.32 72.2 (0.281, 0.678) 137 Example 23 1-82 3.86 68.2 (0.278, 0.682) 141 Example 24 1-83 4.01 60.3 (0.286, 0.692) 132 Example 25 1-86 3.85 69.2 (0.274, 0.672) 138 Example 26 1-87 3.71 77.4 (0.278, 0.678) 139 Example 27 1-88 4.11 67.4 (0.277, 0.674) 151 Example 28 1-113 4.32 62.2 (0.279, 0.674) 143 Example 29 1-114 4.23 69.3 (0.278, 0.677) 153 Example 30 1-117 4.31 68.2 (0.283, 0.677) 141 Example 31 1-119 4.18 66.4 (0.273, 0.678) 149 Example 32 1-120 4.11 67.5 (0.279, 0.681) 146 Example 33 1-121 4.08 68.7 (0.280, 0.679) 132 Example 34 1-122 4.32 70.2 (0.281, 0.678) 137 Example 35 1-123 3.86 68.2 (0.278, 0.682) 141 Example 36 1-124 4.01 60.3 (0.286, 0.692) 132 Example 37 1-126 3.85 68.2 (0.274, 0.672) 138 Example 38 1-127 3.60 72.9 (0.280, 0.673) 173 Example 39 1-128 3.63 79.3 (0.281, 0.678) 169 Example 40 1-130 3.86 78.4 (0.280, 0.678) 166 Example 41 1-133 4.72 63.4 (0.278, 0.673) 142 Example 42 1-138 4.23 67.2 (0.276, 0.672) 139 Example 43 2-1 3.90 79.9 (0.277, 0.676) 148 Example 44 2-2 3.77 73.4 (0.280, 0.674) 167 Example 45 2-5 3.92 79.7 (0.281, 0.672) 178 Example 46 2-7 3.73 71.3 (0.280, 0.674) 178 Example 47 2-14 4.33 69.1 (0.282, 0.679) 142 Example 48 2-16 4.51 67.4 (0.281, 0.684) 153 Example 49 2-17 4.21 69.2 (0.283, 0.681) 146 Example 50 2-18 4.11 63.5 (0.279, 0.681) 146 Example 51 2-22 4.08 66.7 (0.280, 0.679) 132 Example 52 2-23 4.32 72.2 (0.281, 0.678) 137 Example 53 2-37 3.86 68.2 (0.278, 0.682) 141 Example 54 2-41 4.01 60.3 (0.286, 0.692) 132 Example 55 2-42 3.85 69.2 (0.274, 0.672) 138 Example 56 2-43 3.71 77.4 (0.278, 0.678) 139 Example 57 2-44 4.11 67.4 (0.277, 0.674) 151 Example 58 2-45 3.88 74.2 (0.278, 0.677) 160 Example 59 2-47 4.02 62.3 (0.276, 0.671) 152 Example 60 2-54 4.46 66.4 (0.284, 0.687) 149 Example 61 2-59 4.51 68.4 (0.281, 0.684) 153 Example 62 2-62 4.21 70.2 (0.283, 0.681) 146 Example 63 2-63 4.11 67.5 (0.279, 0.681) 146 Example 64 2-64 4.08 68.7 (0.280, 0.679) 132 Example 65 2-66 4.32 70.2 (0.281, 0.678) 137 Example 66 2-70 3.86 68.2 (0.278, 0.682) 141 Example 67 2-79 4.01 60.3 (0.286, 0.692) 132 Example 68 2-85 3.85 68.2 (0.274, 0.672) 138 Example 69 2-88 4.11 67.5 (0.279, 0.681) 146 Example 70 2-106 4.08 68.7 (0.280, 0.679) 132 Example 71 2-117 4.32 70.2 (0.281, 0.678) 137 Example 72 2-121 3.86 68.2 (0.278, 0.682) 141 Example 73 2-124 4.01 60.3 (0.286, 0.692) 132 Example 74 2-125 3.85 68.2 (0.274, 0.672) 138 Example 75 2-161 3.60 72.9 (0.280, 0.673) 173 Example 76 2-162 3.63 79.3 (0.281, 0.678) 169 Example 77 2-164 4.11 67.5 (0.279, 0.681) 146 Example 78 2-165 4.08 68.7 (0.280, 0.679) 132 Example 79 2-166 4.32 70.2 (0.281, 0.678) 137 Example 80 2-167 3.86 68.2 (0.278, 0.682) 141 Example 81 2-170 4.01 60.3 (0.286, 0.692) 132 Example 82 2-182 3.85 68.2 (0.274, 0.672) 138 Example 83 2-187 3.60 72.9 (0.280, 0.673) 173 Example 84 2-190 3.63 79.3 (0.281, 0.678) 169 Example 85 2-194 4.01 60.3 (0.286, 0.692) 132 Example 86 2-195 3.85 68.2 (0.274, 0.672) 138 Example 87 2-196 3.60 72.9 (0.280, 0.673) 173 Example 88 2-199 3.63 79.3 (0.281, 0.678) 169 Example 89 2-201 3.86 78.4 (0.280, 0.678) 166 Example 90 2-203 4.72 63.4 (0.278, 0.673) 142 Example 91 2-204 4.23 67.2 (0.276, 0.672) 139 Example 92 2-206 3.90 79.9 (0.277, 0.676) 148 Example 93 2-208 3.77 73.4 (0.280, 0.674) 167 Example 94 2-218 3.92 79.7 (0.281, 0.672) 178 Example 95 3-1 3.73 71.3 (0.280, 0.674) 178 Example 96 3-2 4.33 69.1 (0.282, 0.679) 142 Example 97 3-30 4.11 67.5 (0.279, 0.681) 146 Example 98 3-41 4.08 68.7 (0.280, 0.679) 132 Example 99 3-42 4.32 70.2 (0.281, 0.678) 137 Example 100 3-43 3.86 68.2 (0.278, 0.682) 141 Example 101 3-48 4.01 60.3 (0.286, 0.692) 132 Example 102 3-58 3.85 68.2 (0.274, 0.672) 138 Example 103 3-61 3.60 72.9 (0.280, 0.673) 173 Example 104 3-62 3.63 79.3 (0.281, 0.678) 169 Example 105 3-63 3.60 72.9 (0.280, 0.673) 173 Example 106 3-66 3.63 79.3 (0.281, 0.678) 169 Example 107 3-81 3.60 72.9 (0.280, 0.673) 173 Example 108 3-90 3.63 79.3 (0.281, 0.678) 169 Example 109 3-94 3.86 78.4 (0.280, 0.678) 166 Example 110 3-112 4.72 63.4 (0.278, 0.673) 142 Example 111 3-122 4.23 67.2 (0.276, 0.672) 139 Example 112 3-123 3.90 79.9 (0.277, 0.676) 148 Example 113 3-161 3.77 73.4 (0.280, 0.674) 167 Example 114 3-163 3.92 79.7 (0.281, 0.672) 178 Example 115 3-166 3.73 71.3 (0.280, 0.674) 178 Example 116 3-168 4.33 69.1 (0.282, 0.679) 142 Example 117 3-201 3.86 68.2 (0.278, 0.682) 141 Example 118 3-203 4.01 60.3 (0.286, 0.692) 132 Example 119 3-210 3.85 68.2 (0.274, 0.672) 138 Example 120 4-1 3.60 72.9 (0.280, 0.673) 173 Example 121 4-2 3.63 79.3 (0.281, 0.678) 169 Example 122 4-3 3.86 78.4 (0.280, 0.678) 166 Example 123 4-4 4.72 63.4 (0.278, 0.673) 142 Example 124 4-10 4.23 67.2 (0.276, 0.672) 139 Example 125 4-33 3.90 79.9 (0.277, 0.676) 148 Example 126 4-40 3.77 73.4 (0.280, 0.674) 167 Example 127 4-49 3.92 79.7 (0.281, 0.672) 178 Example 128 4-50 3.73 71.3 (0.280, 0.674) 178 Example 129 4-51 4.33 69.1 (0.282, 0.679) 142 Example 130 4-55 3.86 78.4 (0.280, 0.678) 166 Example 131 4-113 4.72 63.4 (0.278, 0.673) 142 Example 132 4-128 4.23 67.2 (0.276, 0.672) 139 Example 133 1-1 3.61 72.9 (0.280, 0.673) 170 Example 134 1-17 3.63 79.3 (0.281, 0.678) 165

Looking at the results of Table 6, it can be seen that the organic light emitting device including the compound according to the present invention is excellent in driving voltage, efficiency and lifetime.

Specifically, when comparing the compounds A, B, C, and D of Comparative Examples with the compounds of the present invention, first, in compound A, triazine and dibenzofuran are not directly bonded, and dibenzofuran does not contain an aryl group as a substituent, A carbazole derivative combined with a triazine is different from the present invention. In addition, in the case of compounds B and C, an aryl group is not substituted for dibenzofuran bound to triazine, and compound D does not include the carbazole derivative of the present invention.

On the other hand, it can be seen that the heterocyclic compound of the present invention has excellent thermal stability and luminous efficiency because dibenzofuran/dibenzothiophene/fluorene linked to triazine has an aryl group as a substituent. Specifically, as the aryl group is substituted, the stability of the molecule is increased, and the thermal stability is significantly increased due to the occurrence of steric hindrance of the compound, so that durability and stability of the device are improved, thereby improving the lifespan of the device.

In particular, when comparing the compound D of Comparative Example 4 with the compound of the present invention, the compound containing the condensed carbazole used in the present invention has a structurally appropriate length and strength than the compound having a simple carbazole structure like the comparative compound. The hole mobility is high, and as dibenzofuran/dibenzothiophene/fluorene is substituted with an aryl group, it has high triplet energy due to a steric effect, so that luminous efficiency and lifespan can be improved.

<Experimental Example 2>

1) Fabrication of organic light emitting device

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

The hole injection layer 2-TNATA (4,4', 4"-Tris [2-naphthyl (phenyl) amino] triphenylamine) and the hole transport layer NPB (N, N'-Di( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. The light emitting layer was pre-mixed with one heterocyclic compound of Formula 1 and one compound of Formula 2 as a host, and after pre-mixing, 400 Å was deposited in one park, and the green phosphorescent dopant was Ir(ppy) ₃ at 7% of the deposition thickness of the light emitting layer. Deposited by doping. Thereafter, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transport layer. 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 on the electron injection layer to a thickness of 1,200 Å to form a cathode. An organic electroluminescent device was prepared.

Meanwhile, all organic compounds required for OLED device fabrication were purified by vacuum sublimation under 10 ⁻⁸ to 10 ⁻⁶ torr for each material and used for OLED fabrication.

2) Evaluation of organic light emitting devices

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with McScience's M7000, and with the measurement result, the standard luminance was 6,000 cd through life measurement equipment (M6000) manufactured by McScience. /m ² , T ₉₀ was measured. The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 7.

light emitting layer
compound ratio
(weight ratio) driving voltage
(V) luminous efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Example 135 1-1 : A-3 1:8 4.82 30.3 (0.278, 0.683) 234 Example 136 1-1 : A-3 1:5 4.31 43.2 (0.277, 0.682) 267 Example 137 1-1 : A-3 1:2 3.41 103.4 (0.277, 0.678) 221 Example 138 1-1 : A-3 1:1 3.40 110.3 (0.276, 0.679) 280 Example 139 1-1 : A-3 2:1 3.67 112.1 (0.276, 0.676) 222 Example 140 1-1 : A-3 5:1 4.32 89.7 (0.277, 0.677) 262 Example 141 1-1 : A-3 8:1 4.99 65.3 (0.279, 0.677) 274 Example 142 1-2: A-31 1:2 3.42 101.2 (0.277, 0.677) 293 Example 143 1-2: A-31 1:1 3.44 112.4 (0.277, 0.680) 281 Example 144 1-3: A-16 1:2 3.53 100.2 (0.278, 0.681) 293 Example 145 1-3: A-16 1:1 3.56 108.7 (0.277, 0.682) 282 Example 146 1-17: A-16 1:2 3.38 105.3 (0.281, 0.676) 260 Example 147 1-17: A-16 1:1 3.39 115.3 (0.280, 0.676) 200 Example 148 1-22: A-31 1:2 3.43 104.2 (0.276, 0.679) 355 Example 149 1-22: A-31 1:1 3.43 114.8 (0.275, 0.679) 312 Example 150 1-2: A-97 1:2 3.31 110.4 (0.278, 0.678) 340 Example 151 1-2: A-97 1:1 3.29 117.6 (0.279, 0.677) 342 Example 152 1-2: A-99 1:2 3.88 96.7 (0.275, 0.680) 301 Example 153 1-2 : A-99 1:1 3.78 100.7 (0.274, 0.678) 288 Example 154 1-3 : A-100 1:2 3.77 99.3 (0.276, 0.676) 308 Example 155 1-3 : A-100 1:1 3.78 104.7 (0.274, 0.679) 279 Example 156 2-42: A-34 1:2 3.98 89.7 (0.288, 0.681) 298 Example 157 2-42: A-34 1:1 3.72 101.4 (0.285, 0.680) 282 Example 158 2-44: A-7 1:2 3.01 121.4 (0.276, 0.679) 385 Example 159 2-44: A-7 1:1 3.07 124.7 (0.276, 0.676) 330 Example 160 2-45: A-108 1:2 3.32 112.6 (0.278, 0.681) 340 Example 161 2-45: A-108 1:1 3.42 118.4 (0.275, 0.680) 313 Example 162 2-45: A-102 1:3 3.62 109.4 (0.277, 0.678) 301 Example 163 2-45: A-102 1:2 3.66 116.1 (0.276, 0.677) 285 Example 164 2-45: A-102 1:1.5 3.33 121.3 (0.280, 0.679) 237 Example 165 2-45: A-102 1:1 3.27 118.6 (0.279, 0.678) 281 Example 166 2-161 : A-98 1:2 3.98 89.7 (0.288, 0.681) 298 Example 167 2-161 : A-98 1:1 3.72 101.4 (0.285, 0.680) 282 Example 168 2-164 : A-100 1:2 3.38 105.3 (0.281, 0.676) 260 Example 169 2-164 : A-100 1:1 3.39 115.3 (0.280, 0.676) 200 Example 170 2-194: A-7 1:5 4.31 43.2 (0.277, 0.682) 267 Example 171 2-194: A-7 1:2 3.41 103.4 (0.277, 0.678) 221 Example 172 2-194: A-7 1:1 3.40 110.3 (0.276, 0.679) 280 Example 173 2-195 : A-105 1:3 4.82 30.3 (0.278, 0.683) 234 Example 174 2-195 : A-105 1:2.5 4.31 43.2 (0.277, 0.682) 267 Example 175 2-195 : A-105 1:1 3.41 103.4 (0.277, 0.678) 221 Example 176 3-41: A-100 1:2 3.41 103.4 (0.277, 0.678) 221 Example 177 3-41: A-100 1:1 3.40 110.3 (0.276, 0.679) 280 Example 178 3-42: A-25 1:5 4.31 43.2 (0.277, 0.682) 267 Example 179 3-43: A-98 1:3 3.62 109.4 (0.277, 0.678) 301 Example 180 3-43: A-98 1:2 3.66 116.1 (0.276, 0.677) 285 Example 181 3-43: A-98 1:1.5 3.33 121.3 (0.280, 0.679) 237 Example 182 4-1 : A-2 1:2 3.32 112.6 (0.278, 0.681) 340 Example 183 4-2 : A-98 1:5 4.31 43.2 (0.277, 0.682) 267 Example 184 4-2 : A-98 1:2 3.41 103.4 (0.277, 0.678) 221 Example 185 4-3 : A-99 1:2 3.38 105.3 (0.281, 0.676) 260 Example 186 4-3 : A-99 1:1 3.39 115.3 (0.280, 0.676) 200

Comparing the results of Table 7 with the results of Table 6, it can be seen that the examples containing the compound of Formula 2 show better efficiency and lifespan than the examples containing the heterocyclic compound of Formula 1 alone.

When the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are simultaneously used, it can be confirmed that more excellent effects are exhibited in terms of life, efficiency, and driving voltage characteristics of the organic light emitting device. (exciplex) can be expected to occur.

The exciplex phenomenon is an electron exchange between two molecules of an N-type HOST compound and a P-type HOST compound, releasing energy equivalent to the HOMO level of the donor (P-type HOST) and the LUMO level of the acceptor (N-type HOST) It is a phenomenon that When a donor (P-type HOST) with good hole transport ability and an acceptor (N-type HOST) with good electron transport ability are used as hosts for the light emitting layer, holes are injected into the P-type HOST and electrons are injected into the N-type HOST. Therefore, the driving voltage can be lowered, thereby helping to improve the lifespan.

In the present invention, the heterocyclic compound of Formula 1 was used as an N-type HOST compound, and the compound of Formula 2 was used as a P-type HOST compound.

100: substrate
200: anode
300: organic material 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 (17)

a first electrode; An organic light emitting device comprising a second electrode and one or more organic material layers provided between the first electrode and the second electrode,
An organic light emitting device wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
X and Y are each independently CRR';O; or S,
Z1 to Z3 are each independently N; Or CR", at least one of Z1 to Z3 is N,
L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
l1 is an integer from 1 to 5;
When l1 is 2 or more, L are the same as or different from each other,
Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group,
Ar3, R, R', R", R1 and R2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
a is an integer from 1 to 7;
r1 is an integer from 0 to 6;
r2 is an integer from 0 to 4;
When a, r1 and r2 are each 2 or more, each of Ar2, R1 and R2 is the same as or different from each other,
When a is an integer from 1 to 5, Ar3 is the same as or different from each other. The organic light emitting device of claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
X1 is O; or S,
The definitions of the remaining substituents are the same as those of Formula 1. The method according to claim 1, wherein the Ar3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C30 aryl group of the organic light emitting device. The method according to claim 1, wherein R1 and R2 are each independently hydrogen; Or an organic light emitting element that is deuterium. The organic light emitting device of claim 1, wherein the deuterium content of Chemical Formula 1 is 0% or 10% to 100%. The organic light emitting device of claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

The organic light emitting device of claim 1, wherein the organic material layer including the heterocyclic compound of Formula 1 further comprises a compound of Formula 2 below:
[Formula 2]

In Formula 2,
Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
R21, R22 and R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
L21 and L22 are each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
l21 and l22 are each an integer from 1 to 5,
When l21 and l22 are each 2 or more, each L21 and L22 are the same as or different from each other,
r21 and r22 are each an integer from 0 to 7;
When each of r21 and r22 is 2 or more, each of R21 and R22 is the same as or different from each other. The organic light emitting device of claim 7, wherein the content of deuterium in Formula 2 is 0% or 10% to 100%. The organic light emitting device of claim 7, wherein Chemical Formula 2 is represented by any one of the following compounds:

The organic light emitting device of claim 7, wherein at least one of Chemical Formulas 1 and 2 has a deuterium content greater than 0% and less than 100%. The method of claim 1,
The organic material layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising a heterocyclic compound of formula (1). The method of claim 7,
The organic material layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound of Formula 1 and the compound of Formula 2. The method according to claim 1, wherein the organic light emitting device further comprises 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. device. Heterocyclic compounds of formula 1:
[Formula 1]

In Formula 1,
X and Y are each independently CRR';O; or S,
Z1 to Z3 are each independently N; Or CR", at least one of Z1 to Z3 is N,
L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
l1 is an integer from 1 to 5;
When l1 is 2 or more, L are the same as or different from each other,
Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group,
Ar3, R, R', R", R1 and R2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
a is an integer from 1 to 7;
r1 is an integer from 0 to 6;
r2 is an integer from 0 to 4;
When a, r1 and r2 are each 2 or more, each of Ar2, R1 and R2 is the same as or different from each other,
When a is an integer from 1 to 5, Ar3 is the same as or different from each other. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound according to claim 14 . The method according to claim 15, wherein the composition for the organic material layer of the organic light emitting device further comprises a compound of Formula 2:
[Formula 2]

In Formula 2,
Ar21 and Ar22 are each independently a cyano group; -Si(R101)(R102)(R103); A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
R21, R22 and R101 to R103 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl 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; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
L21 and L22 are each independently a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
l21 and l22 are each an integer from 1 to 5,
When l21 and l22 are each 2 or more, each L21 and L22 are the same as or different from each other,
r21 and r22 are each an integer from 0 to 7;
When each of r21 and r22 is 2 or more, each of R21 and R22 is the same as or different from each other. The method according to claim 16, wherein the weight ratio of the heterocyclic compound of Formula 1 and the compound of Formula 2 in the composition is 1:10 to 10:1 of the composition for an organic layer of an organic light emitting device.

Images