KR20220063432A - Organic light emitting device and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present application provides an organic light emitting device and a composition for an organic material layer. According to the present invention, an organic light emitting device includes a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode. The driving voltage of the organic light emitting device can be lowered, the light efficiency can be improved, or the lifespan characteristics can be improved.

Description

An organic light-emitting device and a composition for an organic material layer of an organic light-emitting device

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

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

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

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

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

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

An object of the present invention is to provide an organic light emitting device and a composition for an organic material layer of the organic light emitting device.

An exemplary embodiment of the present application is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode,

The organic material layer includes a first compound represented by the following formula (1), and provides an organic light emitting device comprising a second compound represented by the following formula (2).

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

Ar1 and Ar2 are the same or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

R1 to R3 are each independently hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted C 1 to C 60 alkyl group,

a and b are each an integer of 0 to 4, when a is 2 or more, R1 is the same as or different from each other, and when b is 2 or more, R2 is the same as or different from each other,

c is an integer of 0 to 5, and when c is 2 or more, R3 are the same as or different from each other,

R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

R23 and R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted silyl group; -P(=O)R101R102; and -NR103R104, wherein R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

r and s are integers from 0 to 7, R23 is the same as or different from each other when r is 2 or more, and R24 is the same as or different from each other when s is 2 or more.

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

By using the heterocyclic compound represented by Formula 1 as the first compound and the heterocyclic compound represented by Formula 2 as the second compound, the organic material layer of the organic light emitting device according to an exemplary embodiment of the present application, The lifespan characteristics of the device may be improved by lowering the driving voltage, improving light efficiency, or thermal stability of the compound.

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

Hereinafter, the present application will be described in detail.

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

In the present specification, "substituted or unsubstituted" refers to a straight-chain or branched alkyl having 1 to 60 carbon atoms; straight-chain or branched alkenyl having 2 to 60 carbon atoms; linear or branched alkynyl having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl having 2 to 60 carbon atoms; monocyclic or polycyclic aryl having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms; -SiRR'R"; -P(=O)RR'; alkylamine having 1 to 20 carbon atoms; monocyclic or polycyclic arylamine having 6 to 60 carbon atoms; and monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms It means that it is substituted or unsubstituted with one or more substituents selected from the group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the exemplified substituents are connected, wherein R, R' and R" are the same as or different from each other, each independently hydrogen; heavy hydrogen; halogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C 6 to C 60 aryl; Or it means that it is a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

In the present specification, "when a substituent is not indicated 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 the exemplary embodiment of the present application, "when a substituent is not indicated in the chemical formula or compound structure" may mean that all positions that may come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in "when a substituent is not indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.

In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, and as an element having a deuteron consisting 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 2H.

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

In the exemplary embodiment of the present application, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents 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 함량 20%라는 것인 하기 구조식으로 표시될 수 있다.That is, in one example,

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

In addition, in the 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 that does not contain a deuterium atom, that is, has 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 in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

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

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

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

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

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

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

In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR104R105R106, R104 to R106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

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

In the present specification, the spiro group is a group including a spiro structure, and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group. Specifically, the spiro group may include any one of the groups of the following structural formula.

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

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, 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, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

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

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

An exemplary embodiment of the present application is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode,

The organic material layer includes a first compound represented by the following formula (1), and provides an organic light emitting device comprising a second compound represented by the following formula (2).

[Formula 1]

[Formula 2]

In Formulas 1 and 2,

Ar1 and Ar2 are the same or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

R1 to R3 are each independently hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted C 1 to C 60 alkyl group,

a and b are each an integer of 0 to 4, when a is 2 or more, R1 is the same as or different from each other, and when b is 2 or more, R2 is the same as or different from each other,

c is an integer of 0 to 5, and when c is 2 or more, R3 are the same as or different from each other,

R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

R23 and R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted silyl group; -P(=O)R101R102; and -NR103R104, wherein R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

r and s are integers from 0 to 7, R23 is the same as or different from each other when r is 2 or more, and R24 is the same as or different from each other when s is 2 or more.

In the compound represented by Formula 1, HOMO (Highest Occupied Molecular Orbital) is delocalized from a biphenyl group to a heterocyclic compound to effectively stabilize holes, and LUMO (Lowest Occupied Molecular Orbital) is delocalized from a triazine to a heterocyclic compound. It can be seen that the electrons are effectively stabilized and thus the efficiency and lifespan are excellent.

In addition, the compound represented by Formula 2 is in the form of a condensed carbazole in which pentagonal to hexagonal rings are condensed through a pi-pi bond. It shows high thermal stability because it has a structure with minimal intramolecular distortion. When a compound exhibiting high thermal stability is used as a material for an organic light emitting device, deformation of the material can be minimized even in high vacuum and high temperature conditions according to the organic light emitting device deposition process, It is possible to improve the durability against deterioration of the device.

Therefore, the compound having the condensed carbazole structure represented by Formula 2 corresponds to a basic structure that can become a material of good lifespan based on low voltage, high efficiency and high thermal stability.

In addition, since the at least one organic material layer includes the heterocyclic compound represented by Formula 1 as the first compound and the heterocyclic compound represented by Formula 2 as the second compound, the driving voltage of the organic light emitting device is reduced It can be lowered or the light efficiency can be improved. From this result, it can be expected that an exciplex phenomenon occurs when both compounds are included in each layer at the same time.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, thereby increasing the internal quantum efficiency of fluorescence to 100%.

Accordingly, the organic light-emitting device according to the present invention has a low driving voltage, excellent light efficiency, or excellent lifespan of the device due to thermal stability. In particular, the lifetime characteristics of the device are excellent.

In the exemplary embodiment of the present application, two or more groups adjacent to each other among R23 and R24 in Formula 2 do not combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring.

By using a compound in which two or more adjacent groups of R23 and R24 among the compounds represented by Formula 2 do not form an aromatic hydrocarbon ring by bonding with each other in the organic light emitting device together with the compound represented by Formula 1, Among the compounds represented, two or more adjacent groups of R23 and R24 combine with each other to form an aromatic hydrocarbon ring. Lowering the driving voltage of the device or , the light efficiency can be improved, or the lifespan characteristics of the device can be improved by the thermal stability of the compound, and in particular, the lifespan characteristics of the device are excellent.

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

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

In the exemplary embodiment of the present application, Ar1 and Ar2 of Formula 1 may be the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present application, Ar1 and Ar2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In an exemplary embodiment of the present application, Ar1 and Ar2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group unsubstituted or substituted with deuterium; Or a carbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.

In the exemplary embodiment of the present application, the bonding position of Ar1 may be represented by the following Chemical Formula A or B.

[Formula A]

[Formula B]

In Formulas A and B, the definition of a substituent is the same as in Formula 1.

In an exemplary embodiment of the present application, R1 to R3 of Formula 1 are each independently hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a and b are each an integer of 0 to 4, when a is 2 or more, R1 is the same as or different from each other, and when b is 2 or more, R2 is the same as or different from each other and c is an integer of 0 to 5, and when c is 2 or more, R3 may be the same as or different from each other.

In an exemplary embodiment of the present application, R1 to R3 of Formula 1 are each independently hydrogen; or deuterium.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

R1 to R3 and a to c have the same definitions as in Formula 1,

X1 and X2 are the same as or different from each other, and each independently O; or S;

Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra is a substituted or unsubstituted C6-C60 aryl group,

R4 to R9 are each independently hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted C 1 to C 60 alkyl group,

d to i are each an integer of 0 to 7, when d is 2 or more, R4 is the same as or different from each other, when e is 2 or more, R5 is the same or different from each other, and when f is 2 or more, R6 is the same as or different from each other, , when g is 2 or more, R7 is the same as or different from each other, when h is 2 or more, R8 is the same as or different from each other, and when i is 2 or more, R9 is the same as or different from each other.

In an exemplary embodiment of the present application, Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra may be a substituted or unsubstituted C6-C60 aryl group.

In an exemplary embodiment of the present application, Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra may be a substituted or unsubstituted C6-C40 aryl group.

In an exemplary embodiment of the present application, Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra may be a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present application, Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra is a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present application, R4 to R9 are each independently hydrogen; or deuterium.

In an exemplary embodiment of the present application, R4 to R9 are all hydrogen.

In an exemplary embodiment of the present application, R4 to R9 are all deuterium.

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

In an exemplary embodiment of the present application, the heterocyclic compound according to Formula 1 may be used as an N-type host.

In an exemplary embodiment of the present application, R23 and R24 of Formula 2 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present application, R23 and R24 are both hydrogen.

In an exemplary embodiment of the present application, R23 and R24 are both deuterium.

In another exemplary embodiment, R21 and R22 in Formula 2 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C 6 to C 40 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In another exemplary embodiment, R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In another exemplary embodiment, R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; Or it may be a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, R21 and R22 are the same as or different from each other, and each independently a silyl group; phenyl group; biphenyl group; terphenyl group; triphenylene group; a fluorenyl group substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms; or a naphthyl group.

According to an exemplary embodiment of the present application, Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto.

In an exemplary embodiment of the present application, the heterocyclic compound according to Formula 2 may be used as a P-type host.

In addition, by introducing various substituents into the structures of Chemical Formulas 1 and 2, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied substances can be synthesized.

In addition, by introducing various substituents into the structures of Chemical Formulas 1 and 2, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material. there is.

On the other hand, the compounds represented by Chemical Formulas 1 and 2 have high glass transition temperature (Tg) and thus excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

The compounds represented by Chemical Formulas 1 and 2 according to an exemplary embodiment of the present application may be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and compounds of Formula 1 or Formula 2 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared based on Preparation Examples to be described later.

In the present specification, the "organic light emitting device" may be expressed in terms such as "organic light emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", "organic electroluminescent device", and the like.

The compounds represented by Chemical Formulas 1 and 2 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In the organic light emitting device of the present application, the organic material layer may include one or more light emitting layers, and the light emitting layer may include the compound as a host material of the light emitting material.

In addition, the organic material layer includes one or more light emitting layers, and the light emitting layer includes the compound represented by Formula 1 and the compound represented by Formula 2 above. In this case, the luminous efficiency and lifespan of the organic light emitting diode are more excellent due to the exciplex phenomenon.

In an exemplary embodiment of the present application, the light emitting layer of the organic light emitting device may be a green light emitting layer, and the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be used as a material for the green light emitting layer. .

In an exemplary embodiment of the present application, the light emitting layer of the organic light emitting device may be a red light emitting layer, and the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be used as a material of the red light emitting layer. .

In an exemplary embodiment of the present application, the light emitting layer of the organic light emitting device may be a blue light emitting layer, and the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be used as a material for the blue light emitting layer. .

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, and at least one of the host materials may include the heterocyclic compound as a host material of the light emitting material.

In the organic light emitting device of the present application, the light emitting layer may be used by pre-mixing two or more host materials. The pre-mixed means that the light emitting layer is mixed with two or more host materials before depositing them on the organic material layer and put it in one park.

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, and the two or more host materials each include one or more P-type host materials and N-type host materials, , At least one of the host material may include the heterocyclic compound as a host material of the light emitting material. In this case, driving, efficiency, and lifespan of the organic light emitting diode may be improved.

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

The organic light emitting device according to an exemplary embodiment of the present application may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the above-described heterocyclic compound.

In addition, another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 above.

In another exemplary embodiment of the present application, the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 in the composition may be 1: 10 to 10: 1, and 1: 8 to 8: It may be 1, it may be 1: 5 to 5: 1, it may be 1: 2 to 2: 1, but is not limited thereto.

Specific details of the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 included in the composition for the organic layer are the same as described above.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

<Preparation Example 1> Preparation of compound 1 (C)

1) Preparation of compound A

(4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl] 3-yl in a one-necked round bottom flask (One neck r.b.f) ) Boronic acid ((4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid) (20g, 51.6 mmol), 4-bromodibenzo [b, d] thiophene (16.2 g, 61.9 mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine) ) palladium (0)) (2.98 g, 2.58 mmol), potassium carbonate (21.3 g, 154.8 mmol), and 1,4-dioxane/water (400 ml/100 ml) ), the mixture was refluxed at 120° C. for 3 hours (h). After completion of the reaction, the resulting solid was washed with distilled water and methanol (MeOH) after the temperature was lowered to room temperature to obtain Compound A (25 g, 92%).

2) Preparation of compound 1 (C)

Compound A (10 g, 19 mmol), dibenzo [b, d] furan-4-ylboronic acid (compound B) in a one neck round bottom flask (One neck r. b. f) ) (4.8g, 22.8mmol), Tetrakis(triphenylphosphine)palladium(0)) (1g, 0.95mmol), Pottasium carbonate (7.8g, 57mmol) , and a mixture of 1,4-dioxane/water (100ml/20ml), and the mixture was refluxed at 120° C. for 3 hours (h). After completion of the reaction, the resulting solid was washed with distilled water and methanol (MeOH) after the temperature was lowered to room temperature to obtain Compound 1 (C) (10 g, 83%).

Compound (C) of Table 1 was synthesized in the same manner as in Preparation Example 1, except that A and B of Table 1 were used instead of Compounds A and B of Preparation Example 1.

<Preparation Example 2> Preparation of compound 25 (F)

1) Preparation of compound D

(4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl] 3-yl in a one-necked round bottom flask (One neck r.b.f) ) Boronic acid ((4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid) (20g, 51.6 mmol), 4-bromodibenzo [b, d] furan (4-bromodibenzo [b, d] furan) (15.3 g, 61.9 mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine) palladium(0)) (2.98g, 2.58mmol), potassium carbonate (21.3g, 154.8mmol), and 1,4-dioxane/water (400ml/100ml) The mixture was refluxed at 120° C. for 3 hours (h). After completion of the reaction, the resulting solid was washed with distilled water and methanol (MeOH) after the temperature was lowered to room temperature to obtain compound D (23 g, 88%).

2) Preparation of compound 25(F)

Compound D (10 g, 19 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (dibenzo [b, d] thiophen-4-ylboronic acid) (compound E) (5.3g, 23.5mmol), Tetrakis(triphenylphosphine)palladium(0)) (1.1g, 0.98mmol), Pottasium carbonate (8.1g, 58.8mmol) , and 1,4-dioxane / water (1,4-dioxane / water) (100ml / 20ml) mixture was refluxed at 120 ℃ 3 hours (h). After completion of the reaction, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol (MeOH) to obtain compound 25(F) (9g, 75%).

Compound (F) of Table 2 was synthesized in the same manner as in Preparation Example 2, except that D and E of Table 2 were used instead of Compounds D and E of Preparation Example 2.

<Preparation Example 3> Synthesis of compound 2-3

1) Preparation of compound 2-3

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

In Preparation Example 3, intermediate G of Table 3 was used instead of 3-bromo-1,1′-biphenyl, and 9-phenyl-9H,9′H-3,3′-bicarbazole was used instead of Table 3 The target compound I was synthesized in the same manner as in Preparation Example 3 except that Intermediate H was used.

Compounds were prepared in the same manner as in Preparation Examples, and the synthesis confirmation results are shown in Tables 4 and 5 below. Table 4 below is a measurement value of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), and Table 5 below is a measurement value of ¹ H NMR (CDCl ₃ , 300Mz).

compound FD-Mass compound FD-Mass One m/z= 657.78 (C45H27N3OS=657.19) 2 m/z= 657.78 (C45H27N3OS=657.19) 3 m/z= 657.78 (C45H27N3OS=657.19) 4 m/z= 657.78 (C45H27N3OS=657.19) 5 m/z= 657.78 (C45H27N3OS=657.19) 6 m/z= 657.78 (C45H27N3OS=657.19) 7 m/z= 657.78 (C45H27N3OS=657.19) 8 m/z= 657.78 (C45H27N3OS=657.19) 9 m/z= 657.78 (C45H27N3OS=657.19) 10 m/z= 657.78 (C45H27N3OS=657.19) 11 m/z= 657.78 (C45H27N3OS=657.19) 12 m/z= 657.78 (C45H27N3OS=657.19) 13 m/z= 657.78 (C45H27N3OS=657.19) 14 m/z= 657.78 (C45H27N3OS=657.19) 15 m/z= 657.78 (C45H27N3OS=657.19) 16 m/z= 657.78 (C45H27N3OS=657.19) 17 m/z= 732.89 (C51H32N5S= 732.23) 18 m/z= 732.89 (C51H32N5S= 732.23) 19 m/z = 808.27 (C57H36N4 = 808.99) 20 m/z= 732.89 (C51H32N5S= 732.23) 21 m/z= 715.84 (C51H33N5=715.27) 22 m/z= 715.84 (C51H33N5=715.27) 23 m/z= 656.20 (C45H28N4S=656.80) 24 m/z = 755.91 (C54H37N5 = 755.30) 25 m/z= 657.78 (C45H27N3OS=657.19) 26 m/z= 657.78 (C45H27N3OS=657.19) 27 m/z= 657.78 (C45H27N3OS=657.19) 28 m/z= 657.78 (C45H27N3OS=657.19) 29 m/z= 657.78 (C45H27N3OS=657.19) 30 m/z= 657.78 (C45H27N3OS=657.19) 31 m/z= 657.78 (C45H27N3OS=657.19) 32 m/z= 657.78 (C45H27N3OS=657.19) 33 m/z= 657.78 (C45H27N3OS=657.19) 34 m/z= 657.78 (C45H27N3OS=657.19) 35 m/z= 657.78 (C45H27N3OS=657.19) 36 m/z= 657.78 (C45H27N3OS=657.19) 37 m/z= 657.78 (C45H27N3OS=657.19) 38 m/z= 657.78 (C45H27N3OS=657.19) 39 m/z= 657.78 (C45H27N3OS=657.19) 40 m/z= 657.78 (C45H27N3OS=657.19) 41 m/z= 716.83 (C51H32N4O=716.23) 42 m/z= 716.83 (C51H32N4O=716.23) 43 m/z = 792.92 (C57H36N4O=792.29) 44 m/z= 716.83 (C51H32N4O=716.23) 45 m/z= 716.83 (C51H32N4O=716.23) 46 m/z = 640.73 (C45H28N4O=640.23) 47 m/z = 640.73 (C45H28N4O=640.23) 48 m/z= 716.83 (C51H32N4O=716.23) 49 m/z= 657.78 (C45H27N3OS=657.19) 50 m/z= 657.78 (C45H27N3OS=657.19) 51 m/z= 657.78 (C45H27N3OS=657.19) 52 m/z= 657.78 (C45H27N3OS=657.19) 53 m/z= 657.78 (C45H27N3OS=657.19) 54 m/z= 657.78 (C45H27N3OS=657.19) 55 m/z= 657.78 (C45H27N3OS=657.19) 56 m/z= 657.78 (C45H27N3OS=657.19) 57 m/z= 657.78 (C45H27N3OS=657.19) 58 m/z= 657.78 (C45H27N3OS=657.19) 59 m/z= 657.78 (C45H27N3OS=657.19) 60 m/z= 657.78 (C45H27N3OS=657.19) 61 m/z= 657.78 (C45H27N3OS=657.19) 62 m/z= 657.78 (C45H27N3OS=657.19) 63 m/z= 657.78 (C45H27N3OS=657.19) 64 m/z= 657.78 (C45H27N3OS=657.19) 65 m/z= 732.89 (C51H32N5S= 732.23) 66 m/z= 732.89 (C51H32N5S= 732.23) 67 m/z = 808.27 (C57H36N4 = 808.99) 68 m/z= 732.89 (C51H32N5S= 732.23) 69 m/z= 715.84 (C51H33N5=715.27) 70 m/z= 715.84 (C51H33N5=715.27) 71 m/z= 656.20 (C45H28N4S=656.80) 72 m/z = 755.91 (C54H37N5 = 755.30) 73 m/z= 657.78 (C45H27N3OS=657.19) 74 m/z= 657.78 (C45H27N3OS=657.19) 75 m/z= 657.78 (C45H27N3OS=657.19) 76 m/z= 657.78 (C45H27N3OS=657.19) 77 m/z= 657.78 (C45H27N3OS=657.19) 78 m/z= 657.78 (C45H27N3OS=657.19) 79 m/z= 657.78 (C45H27N3OS=657.19) 80 m/z= 657.78 (C45H27N3OS=657.19) 81 m/z= 657.78 (C45H27N3OS=657.19) 82 m/z= 657.78 (C45H27N3OS=657.19) 83 m/z= 657.78 (C45H27N3OS=657.19) 84 m/z= 657.78 (C45H27N3OS=657.19) 85 m/z= 657.78 (C45H27N3OS=657.19) 86 m/z= 657.78 (C45H27N3OS=657.19) 87 m/z= 657.78 (C45H27N3OS=657.19) 88 m/z= 657.78 (C45H27N3OS=657.19) 89 m/z= 716.83 (C51H32N4O=716.23) 90 m/z= 716.83 (C51H32N4O=716.23) 91 m/z = 792.92 (C57H36N4O=792.29) 92 m/z= 716.83 (C51H32N4O=716.23) 93 m/z= 716.83 (C51H32N4O=716.23) 94 m/z = 640.73 (C45H28N4O=640.23) 95 m/z = 640.73 (C45H28N4O=640.23) 96 m/z= 716.83 (C51H32N4O=716.23) 2-1 m/z= 484.19 (C36H24N2=484.60) 2-2 m/z= 560.23 (C42H28N2=560.70) 2-3 m/z= 560.23 (C42H28N2=560.70) 2-4 m/z= 560.23 (C42H28N2=560.70) 2-5 m/z= 636.26 (C48H32N2=636.80) 2-6 m/z= 636.26 (C48H32N2=636.80) 2-7 m/z= 636.26 (C48H32N2=636.80) 2-8 m/z= 534.21 (C40H26N2=534.66) 2-9 m/z= 534.21 (C40H26N2=534.66) 2-10 m/z= 600.26 (C45H32N2=600.76) 2-11 m/z= 600.26 (C45H32N2=600.76) 2-12 m/z= 724.29 (C55H36N2=724.91) 2-13 m/z= 724.29 (C55H36N2=724.91) 2-14 m/z= 722.27 (C55H34N2=722.89) 2-15 m/z= 722.27 (C55H34N2=722.89) 2-16 m/z= 634.24 (C48H30N2=634.78) 2-17 m/z= 509.19 (C37H23N3=509.61) 2-18 m/z = 742.28 (C54H38N2Si=743.00) 2-19 m/z= 636.26 (C48H32N2=636.80) 2-20 m/z= 636.26 (C48H32N2=636.80) 2-21 m/z= 636.26 (C48H32N2=636.80) 2-22 m/z= 712.29 (C54H36N2=712.90) 2-23 m/z= 712.29 (C54H36N2=712.90) 2-24 m/z= 712.29 (C54H36N2=712.90) 2-25 m/z= 610.24 (C46H30N2=610.76) 2-26 m/z= 610.24 (C46H30N2=610.76) 2-27 m/z= 676.29 (C51H36N2=676.86) 2-28 m/z= 710.27 (C54H34N2=710.88) 2-29 m/z=585.22 (C43H27N3=585.71) 2-30 m/z= 818.31 (C60H42N2Si=819.10) 2-31 m/z= 636.26 (C48H32N2=636.80) 2-32 m/z= 636.26 (C48H32N2=636.80) 2-33 m/z= 712.29 (C54H36N2=712.90) 2-34 m/z= 712.29 (C54H36N2=712.90) 2-35 m/z= 712.29 (C54H36N2=712.90) 2-36 m/z= 610.24 (C46H30N2=610.76) 2-37 m/z= 610.24 (C46H30N2=610.76) 2-38 m/z= 676.29 (C51H36N2=676.86) 2-39 m/z= 710.27 (C54H34N2=710.88) 2-40 m/z=585.22 (C43H27N3=585.71) 2-41 m/z= 818.31 (C60H42N2Si=819.10) 2-42 m/z= 636.26 (C48H32N2=636.80) 2-43 m/z= 712.29 (C54H36N2=712.90) 2-44 m/z= 712.29 (C54H36N2=712.90) 2-45 m/z= 712.29 (C54H36N2=712.90) 2-46 m/z= 610.24 (C46H30N2=610.76) 2-47 m/z= 610.24 (C46H30N2=610.76) 2-48 m/z= 676.29 (C51H36N2=676.86) 2-49 m/z= 710.27 (C54H34N2=710.88) 2-50 m/z=585.22 (C43H27N3=585.71) 2-51 m/z= 818.31 (C60H42N2Si=819.10) 2-52 m/z= 788.32 (C60H40N2=788.99) 2-53 m/z= 788.32 (C60H40N2=788.99) 2-54 m/z= 788.32 (C60H40N2=788.99) 2-55 m/z= 686.27 (C52H34N2=686.86) 2-56 m/z= 686.27 (C52H34N2=686.86) 2-57 m/z= 752.32 (C57H40N2=752.96) 2-58 m/z= 786.30 (C60H38N2=786.98) 2-59 m/z= 661.25 (C49H31N3=661.81) 2-60 m/z = 894.34 (C66H46N2Si=895.19) 2-61 m/z= 788.32 (C60H40N2=788.99) 2-62 m/z= 788.32 (C60H40N2=788.99) 2-63 m/z= 686.27 (C52H34N2=686.86) 2-64 m/z= 686.27 (C52H34N2=686.86) 2-65 m/z= 752.32 (C57H40N2=752.96) 2-66 m/z= 786.30 (C60H38N2=786.98) 2-67 m/z= 661.25 (C49H31N3=661.81) 2-68 m/z = 894.34 (C66H46N2Si=895.19) 2-69 m/z= 788.32 (C60H40N2=788.99) 2-70 m/z= 686.27 (C52H34N2=686.86) 2-71 m/z= 686.27 (C52H34N2=686.86) 2-72 m/z= 752.32 (C57H40N2=752.96) 2-73 m/z= 786.30 (C60H38N2=786.98) 2-74 m/z= 661.25 (C49H31N3=661.81) 2-75 m/z = 894.34 (C66H46N2Si=895.19) 2-76 m/z= 584.23 (C44H28N2=584.72) 2-77 m/z= 584.23 (C44H28N2=584.72) 2-78 m/z= 650.27 (C49H34N2=650.83) 2-79 m/z= 684.26 (C52H32N2=684.84) 2-80 m/z= 559.20 (C41H25N3=559.67) 2-81 m/z = 792.30 (C58H40N2Si=793.06) 2-82 m/z= 584.23 (C44H28N2=584.72) 2-83 m/z= 650.27 (C49H34N2=650.83) 2-84 m/z= 684.26 (C52H32N2=684.84) 2-85 m/z= 559.20 (C41H25N3=559.67) 2-86 m/z = 792.30 (C58H40N2Si=793.06) 2-87 m/z= 716.32 (C54H40N2=716.93) 2-88 m/z= 750.30 (C57H38N2=750.94) 2-89 m/z= 625.25 (C46H31N3=625.77) 2-90 m/z = 858.34 (C63H46N2Si=859.16) 2-91 m/z= 784.29 (C60H36N2=784.96) 2-92 m/z = 659.24 (C49H29N3=659.79) 2-93 m/z = 892.33 (C66H44N2Si=893.18) 2-94 m/z= 534.18 (C38H22N4=534.62) 2-95 m/z = 767.28 (C55H37N3Si=768.01) 2-96 m/z= 1000.37 (C72H52N2Si2=1001.39) 2-97 m/z=712.88 (C54H36N2=712.29)

compound ¹ H NMR (CDCl ₃ , 300 Mz) 3 δ = 8.45-8.41 (m, 2H), 8.28-8.20 (m, 4H), 7.98 (d, 1H), 7.89 (d, 1H), 7.81 (m, 1H), 7.71-7.32 (m, 18H) 8 δ = 8.45 (d, 1H), 8.28 (d, 2H), 8.11-7.98 (m, 4H), 7.98-7.85 (m, 3H), 7.75-7.32 (m, 17H) 10 δ = 8.45 (d, 1H), 8.28 (d, 2H), 8.00-7.86 (m, 8H), 7.66-7.25 (m, 16H) 12 δ = 8.45 (d, 1H), 8.28 (d, 2H), 8.00-7.98 (m, 3H), 7.89-7.85 (m, 4H), 7.75-7.25 (m, 17H) 23 δ = 8.55(d, 1H), 8.45(d, 1H), 8.28(d, 2H), 8.12-7.94(m, 6H), 7.85(d, 2H), 7.70(s, 1H), 7.57-7.25( m, 15H) 26 δ = 8.45 (d, 1H), 8.28-8.24 (m, 3H), 8.11-8.08 (m, 2H), 7.98 (m, 1H), 7.89-7.81 (m, 4H), 7.70-7.66 (m, 3H) ), 7.57-7.32 (m, 13H) 32 δ = 8.45 (d, 1H), 8.28 (d, 2H), 7.98-7.32 (m, 24H) 34 δ = 8.45 (d, 1H), 8.28 (d, 2H), 8.11-8.08 (m, 2H), 7.98 (m, 2H), 7.89-7.81 (m, 5H), 7.72-7.66 (m, 4H), 7.57-7.25(m, 12H) 44 δ = 8.55 (d, 1H), 8.28 (d, 2H), 8.18 (d, 1H), 7.89-7.25 (m, 28H) 47 δ = 8.55 (d, 1H), 8.28 (d, 2H), 8.12 (d, 1H), 7.95-7.85 (m, 5H), 7.66-7.25 (m, 19H) 53 δ = 8.45(d, 1H), 8.28-8.24(m, 3H), 8.11-7.98(m, 3H), 7.89-7.85(m, 3H), 7,70-7.66(m, 2H), 7.57-7.25 (m, 15H) 55 δ = 8.45(d, 1H), 8.28(d, 2H), 8.11-7.98(m, 4H), 7.89-7.81(m, 4H), 7.72-7.66(m, 3H), 7.52-7.25(m, 13H) ) 59 δ = 8.45 (d, 1H), 8.28-8.24 (m, 3H), 8.00-7.98 (m, 3H), 7.89-7.81 (m, 3H), 7.72-7.66 (m, 4H), 7.57-7.25 (m) , 13H) 65 δ = 8.55(d, 1H), 8.45-8.41(m, 2H), 8.28(m, 2H), 8.20(d, 1H), 7.98-7.85(m, 5H), 7.77(s, 1H), 7.70- 7.69 (m, 2H), 7.57-7.25 (m, 18H) 70 δ = 8.55(d, 1H), 8.45(d, 1H), 8.28(m, 2H), 8.12(m, 1H), 8.00-7.94(m,4H), 7.86-7.85(m,3H), 7.70( s, 1H), 7.57-7.25 (m,15H) 74 δ = 8.45 (d, 1H), 8.28-8.24 (m, 3H), 8.11-8.08 (m, 2H), 7.98 (m, 1H), 7.89-7.81 (m, 4H), 7.70-7.66 (m, 2H) ), 7.57-7.25 (m, 14H) 77 δ = 8.45-8.41 (m, 2H), 8.28 (m, 2H), 7.98-7.80 (m, 7H), 7.66-7.25 (m, 16H) 81 δ = 8.45-8.41 (m, 2H), 8.28 (m, 2H), 7.98 (m, 1H), 7.89-7.80 (m, 5H), 7.58-7.25 (m, 17H) 90 δ = 8.55 (d, 1H), 8.28 (d, 2H), 8.18 (d, 1H), 7.94-7.79 (m, 7H), 7.66-7.25 (m, 21H) 94 δ = 8.55 (d, 1H), 8.28-8.24 (m, 3H), 7.94-7.89 (m, 2H), 7.81 (m, 1H), 7.72-7.25 (m, 21H) 2-3 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) ) 2-4 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) 2-7 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) 2-16 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) 2-31 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) ) 2-32 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) ) 2-34 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) 2-42 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) 2-97 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) )

<Experimental Example> Fabrication of an organic light emitting device

1) Fabrication of an organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer.

After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and 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 deposited thereon to a thickness of 400 Å as follows. For the light emitting layer, the compounds shown in Tables 6 and 7 were used as a host, and Ir(ppy) ₃ (tris(2-phenylpyridine)iridium) as a green phosphorescent dopant was doped with 7wt% of the host based on the weight of the light emitting layer and deposited. After that, 60Å of basocuproine (BCP) was deposited as a hole blocking layer, and 200Å 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) negative electrode is deposited to a thickness of 1200 Å on the electron injection layer to form a cathode, thereby forming an organic electric field. A light emitting device was manufactured.

The compounds shown in Table 7 below were used by pre-mixing two compounds, and the ratios in the table below refer to weight ratios. For example, in the case of Example 1, it means that Compound 1 and Compound 2-3 were pre-mixed in a weight ratio of 1:8 in the light emitting layer.

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

2) Driving voltage and luminous efficiency of organic light emitting device

For the organic light emitting devices of Comparative Examples 1 to 34, Comparative Examples 1-1 to 1-8, and Examples 1 to 71 prepared as described above, electroluminescence (EL) characteristics were measured with M7000 manufactured by Magcius Corporation, and the measurement results T ₉₀ was measured when the reference luminance was 6,000 cd/m ² by using a lifespan measuring device (M6000) manufactured by McScience. The T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The characteristics of the organic light emitting device of the present invention are shown in Tables 6 and 7.

compound drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 One 4.01 70.2 (0.277, 0.669) 174 Comparative Example 2 2 3.62 77.3 (0.281, 0.679) 169 Comparative Example 3 3 3.66 75.2 (0.280, 0.677) 168 Comparative Example 4 4 3.98 72.7 (0.279, 0.676) 154 Comparative Example 5 5 4.64 77.2 (0.272, 0.669) 138 Comparative Example 6 9 4.32 66.4 (0.271, 0.671) 78 Comparative Example 7 13 3.88 67.2 (0.275, 0.672) 158 Comparative Example 8 15 3.74 75.3 (0.279, 0.675) 162 Comparative Example 9 18 3.84 71.4 (0.280, 0.676) 170 Comparative Example 10 19 3.72 72.6 (0.278, 0.672) 169 Comparative Example 11 21 4.53 63.4 (0.283, 0.687) 134 Comparative Example 12 24 4.32 60.2 (0.286, 0.686) 138 Comparative Example 13 25 4.42 67.4 (0.274, 0.678) 102 Comparative Example 14 26 3.99 65.2 (0.279, 0.677) 169 Comparative Example 15 28 3.88 74.2 (0.278, 0.677) 160 Comparative Example 16 32 4.02 63.3 (0.276, 0.671) 152 Comparative Example 17 33 4.46 65.4 (0.284, 0.687) 149 Comparative Example 18 35 4.51 67.4 (0.281, 0.684) 153 Comparative Example 19 37 4.21 69.2 (0.283, 0.681) 146 Comparative Example 20 39 4.11 63.5 (0.279, 0.681) 146 Comparative Example 21 40 4.08 66.7 (0.280, 0.679) 132 Comparative Example 22 42 4.32 72.2 (0.281, 0.678) 137 Comparative Example 23 48 3.86 68.2 (0.278, 0.682) 141 Comparative Example 24 52 4.01 60.3 (0.286, 0.692) 132 Comparative Example 25 65 3.85 69.2 (0.274, 0.672) 138 Comparative Example 26 69 3.71 77.4 (0.278, 0.678) 139 Comparative Example 27 72 4.11 67.4 (0.277, 0.674) 151 Comparative Example 28 75 4.32 62.2 (0.279, 0.674) 143 Comparative Example 29 83 4.23 69.3 (0.278, 0.677) 153 Comparative Example 30 89 4.31 68.2 (0.283, 0.677) 141 Comparative Example 31 92 4.18 66.4 (0.273, 0.678) 149 Comparative Example 32 A 5.72 46.7 (0.273, 0.684) 55 Comparative Example 33 B 5.55 50.2 (0.277, 0.674) 65 Comparative Example 34 C 5.23 59.2 (0.271, 0.686) 43

light emitting layer
compound ratio drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Example 1 1: 2-3 1:8 4.82 30.3 (0.278, 0.683) 234 Example 2 1: 5 4.31 43.2 (0.277, 0.682) 267 Example 3 1: 2 3.41 103.4 (0.277, 0.678) 221 Example 4 1:1 3.40 110.3 (0.276, 0.679) 280 Example 5 2:1 3.67 112.1 (0.276, 0.676) 222 Example 6 5 : 1 4.32 89.7 (0.277, 0.677) 262 Example 7 8:1 4.99 65.3 (0.279, 0.677) 274 Example 8 2: 2-31 1: 2 3.42 101.2 (0.277, 0.677) 293 Example 9 1:1 3.44 112.4 (0.277, 0.680) 281 Example 10 3: 2-16 1: 2 3.53 100.2 (0.278, 0.681) 293 Example 11 1:1 3.56 108.7 (0.277, 0.682) 282 Example 12 17: 2-16 1: 2 3.38 105.3 (0.281, 0.676) 260 Example 13 1:1 3.39 115.3 (0.280, 0.676) 200 Example 14 22: 2-31 1: 2 3.43 104.2 (0.276, 0.679) 355 Example 15 1:1 3.43 114.8 (0.275, 0.679) 312 Example 16 25: 2-6 1: 2 3.31 110.4 (0.278, 0.678) 340 Example 17 1:1 3.29 117.6 (0.279, 0.677) 342 Example 18 20: 2-4 1: 2 3.88 96.7 (0.275, 0.680) 301 Example 19 1:1 3.78 100.7 (0.274, 0.678) 288 Example 20 28: 2-42 1: 2 3.77 99.3 (0.276, 0.676) 308 Example 21 1:1 3.78 104.7 (0.274, 0.679) 279 Example 22 29: 2-34 1: 2 3.98 89.7 (0.288, 0.681) 298 Example 23 1:1 3.72 101.4 (0.285, 0.680) 282 Example 24 32: 2-7 1: 2 3.01 121.4 (0.276, 0.679) 385 Example 25 1:1 3.07 124.7 (0.276, 0.676) 330 Example 26 35: 2-34 1: 2 3.32 112.6 (0.278, 0.681) 340 Example 27 1:1 3.42 118.4 (0.275, 0.680) 313 Example 28 59: 2-42 1: 2 3.62 109.4 (0.277, 0.678) 301 Example 29 1:1 3.66 116.1 (0.276, 0.677) 285 Example 39 1:1 3.33 121.3 (0.280, 0.679) 237 Example 49 1:1 3.27 118.6 (0.279, 0.678) 281 Example 50 17: 2-3 1:1 3.01 121.4 (0.276, 0.679) 215 Example 51 1: 1.5 3.07 124.7 (0.276, 0.676) 230 Example 52 18: 2-7 1: 2 3.32 112.6 (0.278, 0.681) 240 Example 53 1: 2 3.33 112.6 (0.278, 0.681) 243 Example 54 19: 2-3 1:1 3.42 120.4 (0.275, 0.680) 213 Example 55 1: 2 3.12 113.6 (0.278, 0.681) 241 Example 56 20: 2-16 1:1 3.32 119.4 (0.275, 0.680) 215 Example 57 1: 1.5 3.38 129.7 (0.288, 0.681) 218 Example 58 1: 2 3.22 101.4 (0.285, 0.680) 252 Example 59 21: 2-28 1: 2.5 3.21 121.4 (0.276, 0.679) 265 Example 60 1: 2 3.77 109.3 (0.276, 0.676) 1998 Example 61 22: 2-6 1:1 3.78 114.7 (0.274, 0.679) 269 Example 62 1: 1.5 3.01 121.4 (0.276, 0.679) 215 Example 63 1: 2 3.17 114.7 (0.276, 0.676) 230 Example 64 23: 2-35 1: 2.5 3.32 112.6 (0.278, 0.681) 240 Example 65 1: 2 3.77 99.3 (0.276, 0.676) 208 Example 66 1:1 3.78 104.7 (0.274, 0.679) 279 Example 67 24: 2-44 1: 1.5 3.11 121.4 (0.276, 0.679) 215 Example 68 1: 2 3.17 124.7 (0.276, 0.676) 230 Example 69 1: 2.5 3.32 112.6 (0.278, 0.681) 240 Example 70 25: 2-44 1:8 4.22 130.3 (0.278, 0.683) 234 Example 71 1: 5 4.31 143.2 (0.277, 0.682) 267 Comparative Example 1-1 1:D 1: 2 4.86 75.4 (0.280, 0.676) 170 Comparative Example 1-2 1:1 4.72 85.4 (0.284, 0.687) 159 Comparative Example 1-3 24 : E 1: 1.5 4.76 77.4 (0.277, 0.678) 132 Comparative Example 1-4 1: 2 4.76 105.4 (0.284, 0.687) 131 Comparative Example 1-5 22 : F 1: 1.5 4.86 95.4 (0.284, 0.687) 140 Comparative Example 1-6 1: 2 4.86 85.4 (0.284, 0.687) 145 Comparative Example 1-7 32 : G 1: 2 5.16 95.4 (0.284, 0.687) 148 Comparative Example 1-8 1:1 5.26 85.4 (0.284, 0.687) 146

Compounds A to C used in Comparative Examples 32 to 34 are as follows.

In addition, compounds D to G used in Comparative Examples 1-1 to 1-8 are as follows.

In the compound represented by Formula 1 of the present invention, HOMO is delocalized from a biphenyl group to a heterocyclic compound and thus holes can be effectively stabilized, and LUMO is delocalized with a triazine and a heterocyclic compound, so that the electron can be effectively stabilized. .

Therefore, as can be seen in Table 6, it can be confirmed that the organic light emitting devices of Comparative Examples 1 to 31 using the compound represented by Formula 1 are superior to the organic light emitting devices of Comparative Examples 32 to 34 in terms of lifespan and efficiency.

The compound represented by Formula 2 of the present invention is a condensed carbazole compound in which pentagonal to hexagonal rings are condensed through a pi-pi bond. Due to this structure, the compound represented by Formula 2 has a structure in which intramolecular distortion is minimized, thereby exhibiting high thermal stability. When a compound exhibiting high thermal stability is used as a material for an organic light emitting device, deformation of the material can be minimized even in high vacuum and high temperature conditions according to the organic light emitting device deposition process, It is possible to improve the durability against deterioration of the device. That is, the compound having the condensed carbazole structure represented by Chemical Formula 2 corresponds to a basic structure that can become a material of good lifespan based on low voltage, high efficiency and high thermal stability.

When the compounds represented by Formulas 1 and 2 having these characteristics are used as the first compound and the second compound of the organic light emitting device including two or more organic material layers, as can be seen in Table 7, the driving voltage of the organic light emitting device It can be seen that it can be significantly lowered and the light efficiency can be significantly improved. In this case, it can be confirmed that the lifetime of the device is also remarkably improved.

This result shows that when two compounds are included in each layer at the same time, electron exchange between the two molecules emits energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host), exciplex (exciplex). ) is considered to indicate that the phenomenon has occurred. As such, when the exciplex phenomenon between the two molecules occurs, Reverse Intersystem Crossing (RISC) occurs, thereby increasing the internal quantum efficiency of fluorescence to 100%. The light efficiency is excellent, and the lifespan of the device is also excellent due to thermal stability.

As can be seen in Table 7, when comparing 1-8 in Comparative Example 1-1 with Examples, two or more groups adjacent to each other among R23 and R24 in the compound represented by Formula 2 combine with each other to form an aromatic hydrocarbon ring In the compound represented by Formula 2, two or more adjacent groups of R23 and R24 of the compound represented by Formula 2 combine with each other to form an aromatic hydrocarbon ring by using a compound that is not It can be confirmed that the device lifespan characteristics can be improved by lowering the driving voltage of the device, improving the light efficiency, or improving the thermal stability of the compound compared to the case of using the compound represented by Formula 1 together with the organic light emitting device. . In particular, it was confirmed that the lifetime characteristics of the device were excellent.

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

Claims (12)

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode,
The organic material layer comprises a first compound represented by the following formula (1), an organic light emitting device comprising a second compound represented by the following formula (2):
[Formula 1]

[Formula 2]

In Formulas 1 and 2,
Ar1 and Ar2 are the same or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
R1 to R3 are each independently hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted C 1 to C 60 alkyl group,
a and b are each an integer of 0 to 4, when a is 2 or more, R1 is the same as or different from each other, and when b is 2 or more, R2 is the same as or different from each other,
c is an integer of 0 to 5, and when c is 2 or more, R3 are the same as or different from each other,
R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
R23 and R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 6 to C 60 aryl group; a substituted or unsubstituted C 2 to C 60 heteroaryl group; a substituted or unsubstituted silyl group; -P(=O)R101R102; and -NR103R104, wherein R101 to R104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
r and s are integers from 0 to 7, R23 is the same as or different from each other when r is 2 or more, and R24 is the same as or different from each other when s is 2 or more. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group. The organic light emitting diode of claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
R1 to R3 and a to c have the same definitions as in Formula 1,
X1 and X2 are the same as or different from each other, and each independently O; or S;
Y1 and Y2 are the same as or different from each other, and each independently O; S; Or NRa, wherein Ra is a substituted or unsubstituted C6-C60 aryl group,
R4 to R9 are each independently hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted C 1 to C 60 alkyl group,
d to i are each an integer of 0 to 7, when d is 2 or more, R4 is the same as or different from each other, when e is 2 or more, R5 is the same as or different from each other, and when f is 2 or more, R6 is the same or different from each other, , when g is 2 or more, R7 is the same as or different from each other, when h is 2 or more, R8 is the same as or different from each other, and when i is 2 or more, R9 is the same as or different from each other. The method according to claim 1, wherein R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C 6 to C 40 aryl group; or a substituted or unsubstituted C 2 to C 40 heteroaryl group. The method according to claim 1, wherein R1 to R3 are each independently hydrogen; Or deuterium, the organic light emitting device. The method according to claim 1, wherein R23 and R24 are each independently hydrogen; Or deuterium, the organic light emitting device. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

The organic light-emitting device according to claim 1, wherein Chemical Formula 2 is represented by any one of the following compounds:

The organic light emitting device according to claim 1, wherein the organic material layer includes one or more light emitting layers, and the light emitting layer includes the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 above. 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, a hole auxiliary layer, and a hole blocking layer Phosphorus organic light emitting device. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 according to claim 1 . The composition for an organic material layer of an organic light emitting device according to claim 11, wherein the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 in the composition is 1:10 to 10:1.

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