CN112534593A

CN112534593A - Organic light emitting diode

Info

Publication number: CN112534593A
Application number: CN201980051503.2A
Authority: CN
Inventors: 韩美连; 洪性佶; 许瀞午; 许东旭; 李在卓; 梁正勋; 尹喜敬
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-12-07
Filing date: 2019-12-09
Publication date: 2021-03-19
Also published as: WO2020117026A1; KR102469873B1; KR20200070141A

Abstract

The present application relates to an organic light emitting device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic material layers provided between the first electrode and the second electrode.

Description

Organic light emitting diode

Technical Field

The present invention claims priority of korean patent application No. 10-2018-0156860 filed on 7.12.2018 to the korean patent office, the entire contents of which are incorporated herein.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.

There is a continuing demand for the development of new materials for organic light emitting devices as described above.

Disclosure of Invention

Technical subject

The present specification provides an organic light emitting device.

Means for solving the problems

The present specification provides an organic light emitting device, comprising: the organic light emitting device includes an anode, a cathode provided to face the anode, a light emitting layer provided between the anode and the cathode and including a compound represented by chemical formula 1, a hole transport region provided between the anode and the light emitting layer, and an electron transport region provided between the cathode and the light emitting layer and including a compound represented by chemical formula 2.

[ chemical formula 1]

In chemical formula 1, A, B and C are each independently a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, X1 and X2 are each independently O, CR1R2 or NR3, R1 to R3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, adjacent groups among R1 to R3, A, B, and C may be combined with each other to form a substituted or unsubstituted ring,

[ chemical formula 2]

In chemical formula 2, two or more of X4 to X6 are N, and the remainder are CH, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, L is a substituted or unsubstituted aromatic group having a valence of 3, or a substituted or unsubstituted heterocyclic group having a valence of 3, Y is a substituted or unsubstituted polycyclic aryl group, N is 2, and when N is 2, 2Y s are the same as or different from each other.

Effects of the invention

An organic light emitting device using the compound according to an embodiment of the present application can achieve a low driving voltage, high luminous efficiency, and/or a long lifetime.

Drawings

Fig. 1 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole transport region 10, a light-emitting layer 3, an electron transport region 20, and a cathode 4 are sequentially stacked.

Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron adjusting layer 7, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked.

Fig. 3 is an MS spectrum of compound 2-1 according to an embodiment of the present description.

Fig. 4 is an MS spectrum of compound 2-2 according to an embodiment of the present description.

Fig. 5 is an MS spectrum of compounds 2-3 according to an embodiment of the present description.

Fig. 6 is an MS spectrum of compounds 2-4 according to an embodiment of the present description.

Fig. 7 is an MS spectrum of compounds 2-5 according to an embodiment of the present description.

Fig. 8 is an MS spectrum of compounds 2-6 according to an embodiment of the present description.

Fig. 9 is an MS spectrum of compounds 2-9 according to one embodiment of the present description.

Fig. 10 is an MS spectrum of compounds 2-10 according to an embodiment of the present description.

Fig. 11 is an MS spectrum of compounds 2-11 according to an embodiment of the present description.

Fig. 12 is an MS spectrum of compounds 2-12 according to one embodiment of the present description.

Fig. 13 is an MS spectrum of compounds 2-13 according to one embodiment of the present description.

Fig. 14 is an MS spectrum of compounds 2-16 according to an embodiment of the present description.

Fig. 15 is an MS spectrum of compounds 2-17 according to one embodiment of the present description.

Fig. 16 is an MS spectrum of compounds 2-20 according to an embodiment of the present description.

Fig. 17 is an MS spectrum of compounds 2-22 according to one embodiment of the present description.

< description of symbols >

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

7: electronically regulated layer

8: electron injection and transport layer

10: hole transport region

20: electron transport region

Detailed Description

The present specification will be described in more detail below.

The present specification provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein the 1 or more organic layers each include a compound represented by chemical formula 1 or a compound represented by chemical formula 2.

In the present application, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

In the present application, when a part of "including" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, examples of the substituent are described below, but not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from deuterium, a halogen group, cyano, nitro, carbonyl, ester group, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio(s) ((R))

Alkyl thioaxy), substituted or unsubstituted arylthio(s) ((R)

Aryl thio), substituted or unsubstituted alkylsulfonyl(s) ((s)

Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl(s) ((s)

Aryl sufoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted amino, substituted or unsubstituted Aryl phosphino, substituted or unsubstituted phosphinoxide, substituted or unsubstituted Aryl, and substituted or unsubstituted heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples thereof 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-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-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, there are methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, isopentoxy group, n-hexoxy group, 3-dimethylbutoxy group, 2-ethylbutoxy group, n-octoxy group, n-nonoxy group, n-decoxy group, benzyloxy group, p-methylbenzyloxy group and the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different, may be each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30. Specific examples thereof include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.

In the present specification, the amine group may be selected from-NH₂The number of carbon atoms of the alkylamino group, the N-alkylarylamino group, the arylamine group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group and the heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrylfluorenylamino group, and an N-biphenylfluorenylamino group.

In the present specification, an N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted on the N of the amino group.

In this specification, an N-arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group on the N of the amine group.

In the present specification, an N-alkylheteroarylamino group means an amino group substituted with an alkyl group and a heteroaryl group on the N of the amino group.

In the present specification, as an example of the arylamine group, there is a substituted or unsubstituted monoarylamine group or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

And a fluorenyl group, but is not limited thereto.

In the present specification, the above-mentioned fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.

In the case where the above-mentioned fluorenyl group is substituted, it may be

And the like, but is not limited thereto.

In the present specification, the heterocyclic group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the aliphatic hydrocarbon ring is a 2-valent group, and in addition to this, the above description about the cycloalkyl group can be applied.

In the present specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, and arylamino group can be applied to the description about the aryl group.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfonyl group and the alkylamino group can be applied to the above description of the alkyl group.

In the present specification, the heteroaryl group in the heteroaryl group and the heteroarylamino group can be applied to the above description of the heterocyclic group.

In the present specification, the arylene group and the aromatic hydrocarbon ring each have a valence of 2, and in addition to these, the above description of the aryl group can be applied.

In the present specification, heteroarylene and heterocycle are 2-valent groups, and in addition to these, the above description about a heterocyclic group can be applied.

In the present specification, the meaning that adjacent groups are bonded to each other to form a substituted or unsubstituted ring means that adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

In the present specification, the aliphatic hydrocarbon ring as a non-aromatic ring means a ring composed of only carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl, naphthyl, and anthracenyl.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms.

In the present specification, an aromatic heterocyclic ring means an aromatic ring containing 1 or more heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may each be monocyclic or polycyclic.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, the meaning that adjacent groups are bonded to each other to form a substituted or unsubstituted ring means that adjacent groups are bonded to each other to form a five-to eight-membered hydrocarbon ring or a five-to eight-membered heterocyclic ring as described above, may be monocyclic or polycyclic, may be aliphatic, aromatic or a condensed form thereof, and is not limited thereto.

According to an embodiment of the present application, R1 to R3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

Additionally, according to an embodiment of the present application, R1 to R3 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

Further, according to an embodiment of the present application, R1 to R3 are each independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms; aryl substituted or unsubstituted with a group selected from deuterium, alkyl, and trialkylsilyl; or a heterocyclic group.

Additionally, according to an embodiment of the present application, R1 to R3 are each independently methyl; an ethyl group; isopropyl group; a tertiary butyl group; phenyl substituted or unsubstituted with a group selected from deuterium, alkyl, and trialkylsilyl; a biphenyl group; or a dibenzofuranyl group.

According to an embodiment of the present application, groups adjacent to each other among R1 to R3, A, B and C may be combined to form a substituted or unsubstituted ring.

In addition, according to an embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C may be combined to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

In addition, according to an embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C may be combined to form a substituted or unsubstituted hydrocarbon ring of carbon number 6 to 60 or a substituted or unsubstituted heterocyclic ring of carbon number 2 to 60.

In addition, according to an embodiment of the present application, groups adjacent to each other among R1 to R3, A, B, and C may be combined to form a substituted or unsubstituted hydrocarbon ring of 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 carbon atoms.

According to an embodiment of the present application, the chemical formula 1 may be represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the chemical formula 1-1,

A. b and C are as defined in claim 1,

r 'and R' are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

groups adjacent to each other in R', R ", A, B, and C may combine to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

According to an embodiment of the present application, the compound represented by the above chemical formula 1 may include at least one or more deuterium.

According to an embodiment of the present application, A, B and C are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

In one embodiment of the present application, the A, B and C are a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 3 to 60 carbon atoms.

In one embodiment of the present invention, the A, B and C are a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 3 to 30 carbon atoms.

According to an embodiment of the present application, A, B and C are each independently a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

According to an embodiment of the present application, A, B and C are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted carbazole, or substituted or unsubstituted phenanthrene.

According to an embodiment of the present application, the chemical formula 1 may be represented by the following chemical formula 3.

[ chemical formula 3]

In the above chemical formula 3, X1 and X2 are the same as defined in chemical formula 1,

z1 to Z3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring,

a and b are each an integer of 1 to 4,

c is an integer of 1 to 3,

when a to c are 2 or more, the structures in parentheses are the same as or different from each other.

According to an embodiment of the present application, each of Z1 to Z3 is independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present application, Z1 to Z3 are each independently hydrogen; deuterium; diarylamine substituted or unsubstituted with a group selected from deuterium, diarylamine, and carbazolyl; a phenyl group; a biphenyl group; a methyl group; a tertiary butyl group; carbazolyl substituted or unsubstituted with a group selected from aryl and carbazolyl; or trialkylsilyl groups, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present specification, when Z1 to Z3 and R1 to R3 each independently combine adjacent groups with each other to form a substituted or unsubstituted ring, the adjacent groups may be directly bonded to each other or connected by any one of the following structures to form a ring.

In the above-described structure, the first and second electrodes,

a1 through A24 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a1 to a11 are each an integer of 0 to 4,

a12 is an integer of 0 to 6,

indicates the position of the substitution.

According to an embodiment of the present application, the above chemical formula 1 may be represented by any one of the following chemical formulas 3-1 to 3-3.

[ chemical formula 3-1]

[ chemical formula 3-2]

[ chemical formulas 3-3]

In the above chemical formulas 3-1 to 3-3,

x3 is a direct bond, O, CR11R12 or NR13,

z11 to Z19 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring,

z11, z12 and z17 are each an integer of 1 to 4,

z13, z14, z15, z16, z18 and z19 are each an integer of 1 to 3,

z11 to z19 are 2 or more, the structures in parentheses are the same as or different from each other,

r4 to R8 and R11 to R13 are each independently a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, R4 to R8 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, R4 to R8 are each independently methyl; an ethyl group; isopropyl group; a tertiary butyl group; phenyl substituted or unsubstituted with a group selected from deuterium, alkyl, and trialkylsilyl; a biphenyl group; or a dibenzofuranyl group.

According to an embodiment of the present application, R11 to R13 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an embodiment of the present application, R11 to R13 are each independently hydrogen, deuterium, methyl or phenyl.

According to an embodiment of the present application, each of Z11 to Z19 is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present application, Z11 to Z19 are each independently hydrogen; deuterium; diarylamine substituted or unsubstituted with a group selected from deuterium, diarylamine, and carbazolyl; a phenyl group; a biphenyl group; a methyl group; a tertiary butyl group; carbazolyl substituted or unsubstituted with a group selected from aryl and carbazolyl; or trialkylsilyl groups, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present application, when adjacent groups of Z11 to Z19 are combined with each other to form a substituted or unsubstituted ring, each may independently form a substituted or unsubstituted indole ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

According to an embodiment of the present application, when adjacent groups of Z11 to Z19 are bonded to each other to form a substituted or unsubstituted ring, an indole ring substituted or unsubstituted with an aryl group, a benzene ring substituted or unsubstituted with an alkyl group, or a naphthalene ring may be formed independently of each other.

According to an embodiment of the present application, when adjacent groups of Z11 to Z19 are bonded to each other to form a substituted or unsubstituted ring, an indole ring substituted or unsubstituted with a phenyl group, a benzene ring substituted or unsubstituted with a tert-butyl group, or a naphthalene ring may be formed independently of each other.

According to an embodiment of the present application, the chemical formula 1 is selected from the following structural formulas.

An organic light emitting device according to an embodiment of the present application includes a compound represented by the following chemical formula 2.

[ chemical formula 2]

In the chemical formula 2, the first and second organic solvents,

at least one of X4 to X6 is N, the remainder are CR',

ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l is a direct bond, a substituted or unsubstituted aryl group having a valence of n +1, or a substituted or unsubstituted heterocyclic group having a valence of n +1,

y is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

r' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n is 1 or 2, and n is a hydrogen atom,

when n is 2, 2Y's are the same as or different from each other.

According to an embodiment of the present application, at least one of X4 to X6 is N, the remainder are CR'.

According to an embodiment of the present application, two or more of X4 to X6 are N, and the others are CH.

According to an embodiment of the present application, two of X4 to X6 are N, and the rest are CH.

According to an embodiment of the present application, X4 to X6 are N.

According to an embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted pyrenyl group.

According to an embodiment of the present application, Ar1 and Ar2 are each independently phenyl, biphenyl, naphthyl, phenanthryl, alkyl-substituted fluorenyl, dibenzofuranyl, dibenzothiophenyl, or pyrenyl.

According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted aryl group having a valence of n +1, or a substituted or unsubstituted heterocyclic group having a valence of n + 1.

According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted aryl group having a valence of n +1 and having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having a valence of n +1 and having 2 to 60 carbon atoms.

According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted aryl group having a valence of n +1 and having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having a valence of n +1 and having 2 to 30 carbon atoms.

According to an embodiment of the present application, L is a direct bond, a substituted or unsubstituted aryl group having a valence of n +1 and having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having a valence of n +1 and having 2 to 15 carbon atoms.

According to an embodiment of the present application, L is a substituted or unsubstituted aryl group having a valence of 3, or a substituted or unsubstituted heterocyclic group having a valence of 3.

According to an embodiment of the present application, L is a substituted or unsubstituted aryl group having a valence of 3 and having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having a valence of 3 and having 2 to 15 carbon atoms.

According to an embodiment of the application, L is a substituted or unsubstituted aryl group having a valence of 3.

According to an embodiment of the present application, L is a substituted or unsubstituted aryl group having a valence of 3 and having 2 to 15 carbon atoms.

According to an embodiment of the present application, L is a substituted or unsubstituted phenyl group having a valence of 3, or a substituted or unsubstituted biphenyl group having a valence of 3.

According to an embodiment of the present application, L is a 3-valent phenyl group, or a 3-valent biphenyl group.

According to an embodiment of the present application, Y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group. Here, polycyclic means a state in which 2 or more rings are condensed.

According to an embodiment of the application, Y is a substituted or unsubstituted bicyclic to pentacyclic aryl group.

According to an embodiment of the application, Y is a substituted or unsubstituted bicyclic to tetracyclic aryl.

According to an embodiment of the present application, Y is a substituted or unsubstituted bicyclic to tricyclic aryl.

According to an embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group of 6 to 60 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group of 6 to 30 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group of 6 to 15 carbon atoms.

According to an embodiment of the present application, Y is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present application, n is 1 or 2.

According to an embodiment of the present application, n is 2.

According to an embodiment of the present application, when n is 2,2 ys are identical to each other.

According to an embodiment of the present application, when n is 2,2 ys are different from each other.

According to an embodiment of the present application, R' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, R' is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the application, R' is hydrogen or deuterium.

According to an embodiment of the present application, the chemical formula 2 is selected from the following structural formulas.

For example, the compound of the above chemical formula 1 may produce a core structure as shown in the following reaction formula 1, and the compound of the above chemical formula 2 may produce a core structure as shown in the following reaction formula 2. The substituents may be bonded by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.

[ reaction formula 1]

In the above reaction formula 1, A, B and C are as defined in chemical formula 1,

d and E are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring, A₁To A₃Each a functional group capable of undergoing a coupling reaction with an amine.

The Amine (Amine) compound and the halogenated aromatic ring compound are subjected to a Coupling reaction (Coupling reaction) using a Pd catalyst under a nitrogen atmosphere to obtain a compound having a structure of formula a.

The same equivalent of another amine compound as in chemical formula a was added, and a compound having a structure of chemical formula B was obtained by a coupling reaction using a Pd catalyst. In addition, in a flask containing the compound having the structure of formula B, t-Butyl Lithium (t-Butyl Lithium) solution was added at-80 ℃. After stirring for about 30 minutes, boron tribromide is added, and the temperature is raised to room temperature. Then, the mixture is cooled to 0 ℃ again, N-diisopropylethylamine is added, and then the mixture is heated to 120 ℃ and heated and stirred. After the reaction is completed, it is cooled to room temperature, and then passes through a purification process, thereby obtaining the core structure of chemical formula 1-1-1.

[ reaction formula 2]

In the above reaction formula 2, X4 to X6, L, n, Ar1 and Ar2 are the same as defined in chemical formula 2.

In the above reaction scheme 2, a linker in the form of a boronic acid (boronic acid) or a boronic ester (boronate) is used to link a triazine (triazine) compound: (

(link)) was subjected to a coupling reaction using Pd as a catalyst to obtain a compound having a structure of formula C.

The same equivalent of bis (pinacolato) diboron as in formula C was added to bis (pinacolato) diboron

In an alkane solution (dioxane solvent), a boronation (borylation) reaction was performed using a base KOAc and Pd as catalysts to obtain a compound having a structure of formula D. In addition, a core structure of chemical formula 2 is obtained by a coupling reaction of a compound having a structure of chemical formula D with Y.

The organic layer of the organic light-emitting device of the present application may be formed of a single layer structure, or may be formed of a multilayer structure in which 2 or more organic 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 an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.

In one embodiment of the present application, the organic layer may include a layer including the compound represented by chemical formula 2 between the first electrode and the light emitting layer.

In one embodiment of the present application, the organic layer may include a layer including the compound represented by chemical formula 2 between the second electrode and the light emitting layer.

In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by chemical formula 2.

In one embodiment of the present application, the organic layer includes a light emitting layer including the compound represented by the chemical formula 1.

In one embodiment of the present application, the organic light emitting device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

The light emitting layer may include a compound represented by chemical formula 1. Specifically, the light emitting layer may include a host and a dopant containing the chemical formula 1.

The luminescent layer can be wrappedContaining a compound represented by chemical formula 1 as a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, dibenzofuran, a dibenzofuran derivative, dibenzothiophene, a dibenzothiophene derivative, a ladder-type furan compound

Pyrimidine derivatives, etc., but are not limited thereto.

In an embodiment of the present application, the weight ratio of the host to the dopant may be 90:10 to 99: 1. Specifically, it may be 90:10, 91:9, 92:8, 93:7, 94:6, 95:5, 96:4, 97:3, 98:2 or 99:1, and preferably, it may be 95:5, but is not limited thereto.

In one embodiment of the present application, the organic layer including the compound of the

above chemical formula

1 or 2 has a thickness of each

To

In one embodiment of the present application, the host includes an anthracene derivative. In this case, the anthracene derivative may be substituted or unsubstituted anthracene, and adjacent substituents among the substituents substituted in anthracene may be bonded to each other to form a substituted or unsubstituted ring.

In one embodiment of the present application, the host includes a compound represented by the following chemical formula 4.

[ chemical formula 4]

In the above-mentioned chemical formula 4,

l101 and L102, which may be the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

r101 to R108 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,

ar101 and Ar102 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or is linked to an adjacent substituent to form a substituted or unsubstituted ring,

m1 and m2 are each an integer of 0 to 5,

when m1 is 2 or more, L101 s may be the same as or different from each other,

when m2 is 2 or more, L102 s may be the same as or different from each other.

In one embodiment of the present application, the host contains a compound represented by any one of the following structures.

In one embodiment of the present application, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and 1 or more organic material layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode. In one embodiment of the present application, the 1 or more organic layers may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

In one embodiment of the present application, the organic light emitting device may include an anode, a cathode facing the anode, a light emitting layer between the anode and the cathode and including a compound represented by chemical formula 1, a hole transport region between the anode and the light emitting layer, and an electron transport region between the cathode and the light emitting layer and including a compound represented by chemical formula 2.

In one embodiment of the present application, the hole transport region includes 1 or more organic layers between the anode and the light-emitting layer, and serves to receive holes from the anode and transfer the holes to the light-emitting layer. The hole transport region may include at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole adjusting layer, and an electron blocking layer.

In one embodiment of the present application, the electron transport region includes 1 or more organic layers between the cathode and the light-emitting layer, and serves to receive holes from the cathode and transfer the holes to the light-emitting layer. The electron transport region may include at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron adjustment layer, and a hole blocking layer.

The electron transport region may include an electron adjusting layer, an electron injecting layer, an electron transporting layer, or an electron injecting and transporting layer, and the electron adjusting layer, the electron injecting layer, the electron transporting layer, or the electron injecting and transporting layer may include the compound represented by chemical formula 2.

In one embodiment of the present application, the electron transport region includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the compound represented by chemical formula 2. Specifically, in one embodiment of the present application, the compound represented by chemical formula 2 may be contained in 1 of the 2 or more electron transport layers, or may be contained in 2 or more electron transport layers.

In one embodiment of the present application, when the compound represented by chemical formula 2 is included in the respective electron transport layers of 2 or more layers, materials other than the compound may be the same or different from each other.

In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 and 2 illustrate a structure of an organic light emitting device according to an embodiment of the present application.

Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole transport region 10, a light emitting layer 3, an electron transport region 20, and a cathode 4 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 is contained in the above light emitting layer 3, and the compound represented by the above chemical formula 2 may be contained in the electron transporting region 20.

Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron adjusting layer 7, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 is contained in the above light emitting layer 3, and the compound represented by the above chemical formula 2 may be contained in the electron adjusting layer 7 or the electron injecting and transporting layer 8.

The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the compound of the present application, i.e., the above-described compound.

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above compound, i.e., the compound represented by the above chemical formula 1.

For example, the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

In addition, the compound of chemical formula 1 may be used to form an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

In one embodiment of the present disclosure, the first electrode is an anode (anode), and the second electrode is a cathode (cathode).

In another embodiment, the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; hexanenitrile hexaazatriphenylene series organic matter; quinacridone (quinacridone) -based organic compounds; perylene (perylene) -based organic compounds; anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting layer contains another light-emitting substance in addition to the compound represented by chemical formula 1. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (di)merized styryl) compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the cathode or the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is a material that can inject electrons well from the cathode and transfer the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium, samarium, etc., in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the cathode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The hole blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole injection layer. Specifically, there are

An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting device according to the present application may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

Modes for carrying out the invention

The fabrication of the organic light emitting device comprising the compounds represented by the

above chemical formulas

1 and 2 is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.

Production example 1: chemical formula 1)

< production example 1-1> Synthesis of Compound 1-1

1) Synthesis of Compound 1-1-A

Under a nitrogen atmosphere, N-methylaniline (30.0g), 1-bromo-2, 3-dichlorobenzene (63g), Pd (tBu)₃P)₂A flask (0.29g), NaOtBu (53.8g) and Xylene (500ml) was heated at 80 ℃ with stirring for 4 hours, then heated to 120 ℃ with stirring and further stirred for 3 hours. Cooling the reaction liquidAfter the mixture was cooled to room temperature, water and ethyl acetate were added to separate the mixture. Subsequently, the residue was purified by silica gel column chromatography (developing solution: toluene/heptane 1/20 (volume ratio)), whereby 2, 3-dichloro-N-methyl-N-phenylaniline (64.0g) was obtained.

tBu here means tert-butyl.

MS[M+H]⁺＝252

2) Synthesis of Compound 1-1-B

Under nitrogen atmosphere, 2, 3-dichloro-N-methyl-N-phenylaniline (20.0g), N-methylaniline (8.5g), Pd (t-Bu)₃P)₂A flask of (0.08g), NaOtBu (15.2g) and xylene was heated at 120 ℃ with stirring for 1 hour. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to separate the reaction mixture. Subsequently, the mixture was purified by a silica gel short-path chromatography column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (the volume ratio of heptane/ethyl acetate was 1), thereby obtaining 2-chloro-N1, N3-dimethyl-N1, N3-diphenylbenzene-1, 3-diamine (23.2 g).

MS[M+H]⁺＝323

3) Synthesis of Compound 1-1

1.6M t-butyllithium pentane solution (48.4ml) was added under a nitrogen atmosphere at-30 ℃ in a flask containing 2-chloro-N1, N3-dimethyl-N1, N3-diphenylbenzene-1, 3-diamine (25.0g) and t-butylbenzene (130 ml). After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 1 hour, and then a component having a lower boiling point than tert-butylbenzene was distilled off under reduced pressure. Cooled to-30 ℃, boron tribromide (10.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 0.5 hour. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (12.8ml) was added, and stirred at room temperature until the generated heat was cooled, then warmed to 120 ℃ and stirred with heating for 2 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added thereto, followed by separating with ethyl acetate. Then, the mixture was purified by a silica gel short-path chromatography column (developing solution: heated chlorobenzene). After washing with refluxing heptane and refluxing ethyl acetate, the compound represented by chemical formula 1-1 (16.3g) was obtained by reprecipitation from chlorobenzene.

MS[M+H]⁺＝297

< production example 1-2> Synthesis of Compound 1-2

1) Synthesis of Compound 1-2-A

In a nitrogen atmosphere, diphenylamine (37.5g), 1-bromo-2, 3-dichlorobenzene (50.0g), Pd (t-Bu) were charged₃P)₂A flask of (0.58g), NaOtBu (32.0g) and xylene (500ml) was heated at 80 ℃ with stirring for 4 hours, then heated to 120 ℃ with stirring for another 3 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to separate the reaction mixture. Subsequently, the residue was purified by silica gel column chromatography (developing solution: toluene/heptane 1/20 (volume ratio)), whereby 2, 3-dichloro-N, N-diphenylaniline (63.0g) was obtained.

MS[M+H]⁺＝314

2) Synthesis of Compound 1-2-B

Under nitrogen atmosphere, 2, 3-dichloro-N, N-diphenylaniline (16.2g), bis ([1,1' -biphenyl) were charged]-4-yl) amine (15.0g), Pd (t-Bu)₃P)₂A flask of (0.22g), NaOtBu (6.7g) and xylene (150ml) was heated at 120 ℃ with stirring for 1 hour. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to separate the reaction mixture. Subsequently, the gel was purified by a silica gel short-path chromatography column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (the volume ratio of these was heptane/ethyl acetate ═ 1), to remove impurities from the gelThus, N1, N1-bis ([1,1' -biphenyl ] is obtained]-4-yl) -2-chloro-N3, N3-diphenylbenzene-1, 3-diamine (22.0 g).

MS[M+H]⁺＝599

3) Synthesis of Compound 1-2

1.6M t-butyllithium pentane solution (48.4ml) was added under a nitrogen atmosphere at-30 ℃ in a flask charged with N1, N1-bis ([1,1' -biphenyl ] -4-yl) -2-chloro-N3, N3-diphenylbenzene-1, 3-diamine (22.0g) and t-butylbenzene (130 ml). After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 1 hour, and then a component having a lower boiling point than tert-butylbenzene was distilled off under reduced pressure. Cooled to-30 ℃, boron tribromide (6.2ml) was added, the temperature was raised to room temperature, and stirring was carried out for 0.5 hour. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (12.8ml) was added, and stirred at room temperature until the generated heat was cooled, then warmed to 120 ℃ and stirred with heating for 2 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added thereto, followed by separating with ethyl acetate. Then, the mixture was purified by a silica gel short-path chromatography column (developing solution: heated chlorobenzene). After washing with refluxing heptane and refluxing ethyl acetate, the compound represented by chemical formula 1-2 (11.2g) was obtained by further reprecipitation from chlorobenzene.

MS[M+H]⁺＝573

< production example 3> Synthesis of Compounds 1 to 3

1) Synthesis of Compound 1-3-A

Compound 1-3-a was produced by the same method as compound 1-1-a except that bis ([1,1' -biphenyl ] -3-yl) amine was used instead of N-methylaniline.

MS[M+H]⁺＝466

2) Synthesis of Compound 1-3-B

Compound 1-3-B was produced by the same method as compound 1-1-B except that [ compound 1-3-a ] was used instead of [ compound 1-1-a ], and N1, N1, N3-triphenylbenzene-1, 3-diamine was used instead of N-methylaniline.

MS[M+H]⁺＝614

3) Synthesis of Compounds 1-3

Compound 1-3 was produced by the same method as compound 1-1, except that [ compound 1-3-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝740

< production examples 1-4> Synthesis of Compounds 1-4

1) Synthesis of Compound 1-4-A

Compound 1-4-a was produced in the same manner as compound 1-1-a, except that 1-bromo-2, 3-dichloro-5-methylbenzene was used instead of 1-bromo-2, 3-dichlorobenzene and 3, 5-di-tert-butyl-N- (3- (tert-butyl) phenyl) aniline was used instead of N-methylaniline.

MS[M+H]⁺＝496

2) Synthesis of Compound 1-4-B

Compound 1-4-B was produced by the same method as compound 1-1-B, except that [ compound 1-4-a ] was used instead of [ compound 1-1-a ] and bis (4- (tert-butyl) phenyl) amine was used instead of N-methylaniline.

MS[M+H]⁺＝741

3) Synthesis of Compounds 1-4

Compound 1-4 was produced by the same method as compound 1-1, except that [ compound 1-4-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝715

< production examples 1-5> Synthesis of Compounds 1-5

1) Synthesis of Compound 1-5-A

Compound 1-5-a was produced by the same method as compound 1-1-a except that N, 9-diphenyl-9H-carbazol-2-amine was used instead of N-methylaniline.

MS[M+H]⁺＝479

2) Synthesis of Compound 1-5-B

Compound 1-5-B was produced in the same manner as Compound 1-1-B, except that [ Compound 1-5-A ] was used in place of [ Compound 1-1-A ] and N1, N1, N3-triphenylbenzene-1, 3-diamine was used in place of N-methylaniline.

MS[M+H]⁺＝779

3) Synthesis of Compounds 1-5

Compound 1-5 was produced by the same method as compound 1-1, except that [ compound 1-5-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝753

< production examples 1-6> Synthesis of Compounds 1-6

1) Synthesis of Compound 1-6-A

Compound 1-6-A was produced in the same manner as Compound 1-1-A except that N-phenylnaphthalene-2-amine was used instead of N-methylaniline.

MS[M+H]⁺＝364

2) Synthesis of Compound 1-6-B

Compound 1-6-B was produced in the same manner as Compound 1-1-B except that [ Compound 1-6-A ] was used in place of [ Compound 1-1-A ] and diphenylamine was used in place of N-methylaniline.

MS[M+H]⁺＝497

3) Synthesis of Compounds 1-6

Compound 1-6 was produced by the same method as compound 1-1, except that [ compound 1-6-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝471

< production examples 1-7> Synthesis of Compounds 1-7

1) Synthesis of Compound 1-7-A

Compound 1-7-a was produced in the same manner as compound 1-1-a except that 9- (3-bromo-4, 5-dichlorophenyl) -9H-carbazole was used instead of 1-bromo-2, 3-dichlorobenzene and 3- (tert-butyl) -N- (4- (tert-butyl) phenyl) aniline was used instead of N-methylaniline.

MS[M+H]⁺＝591

2) Synthesis of Compound 1-7-B

Compound 1-7-B was produced by the same method as compound 1-1-B, except that [ compound 1-7-a ] was used instead of [ compound 1-1-a ] and bis (4- (tert-butyl) phenyl) amine was used instead of N-methylaniline.

MS[M+H]⁺＝836

3) Synthesis of Compounds 1-7

Compound 1-7 was produced by the same method as compound 1-1, except that [ compound 1-7-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝810

< production examples 1-8> Synthesis of Compounds 1-8

1) Synthesis of Compound 1-8-A

Compound 1-8-a was produced in the same manner as compound 1-1-a, except that 3-bromo-4, 5-dichloro-N, N-diphenylaniline was used instead of 1-bromo-2, 3-dichlorobenzene and 3- (tert-butyl) -N- (4- (tert-butyl) phenyl) aniline was used instead of N-methylaniline.

MS[M+H]⁺＝593

2) Synthesis of Compound 1-8-B

Compound 1-8-B was produced in the same manner as compound 1-1-B, except that [ compound 1-8-a ] was used instead of [ compound 1-1-a ] and 3- (tert-butyl) -N- (4- (tert-butyl) phenyl) aniline was used instead of N-methylaniline.

MS[M+H]⁺＝838

3) Synthesis of Compounds 1-8

Compound 1-8 was produced by the same method as Compound 1-1, except that [ Compound 1-8-B ] was used instead of [ Compound 1-1-B ].

MS[M+H]⁺＝812

< production examples 1-9> Synthesis of Compounds 1-9

1) Synthesis of Compound 1-9-A

Compound 1-9-a was produced by the same method as compound 1-1-a except that N-phenyldibenzo [ b, d ] furan-3-amine was used instead of N-methylaniline.

MS[M+H]⁺＝404

2) Synthesis of Compound 1-9-B

Compound 1-9-B was produced in the same manner as Compound 1-1-B, except that [ Compound 1-9-A ] was used in place of [ Compound 1-1-A ] and N-phenyldibenzo [ B, d ] furan-3-amine was used in place of N-methylaniline.

MS[M+H]⁺＝627

3) Synthesis of Compounds 1-9

Compound 1-9 was produced by the same method as compound 1-1, except that [ compound 1-9-B ] was used instead of [ compound 1-1-B ].

MS[M+H]⁺＝601

< production examples 1-10> Synthesis of Compounds 1-10

1) Synthesis of Compound 1-10-A

Compound 1-10-a was produced by the same method as compound 1-1-a except that N-phenyl-4- (trimethylsilyl) aniline was used instead of N-methylaniline and 3-bromo-4, 5-dichloro-N, N-diphenylaniline was used instead of 1-bromo-2, 3-dichlorobenzene.

MS[M+H]⁺＝553

2) Synthesis of Compound 1-10-B

Compound 1-10-B was produced in the same manner as Compound 1-1-B, except that [ Compound 1-10-A ] was used in place of [ Compound 1-1-A ] and N-phenyl-4- (trimethylsilyl) aniline was used in place of N-methylaniline.

MS[M+H]⁺＝758

3) Synthesis of Compounds 1-10

Compounds 1 to 10 were produced by the same method as Compound 1-1, except that [ Compound 1-10-B ] was used instead of [ Compound 1-1-B ].

MS[M+H]⁺＝732

< production examples 1-11> Synthesis of Compounds 1-11

1) Synthesis of Compound 1-11-A

Compound 1-11-a was produced in the same manner as compound 1-1-a, except that 4- (tert-butyl) -N-phenylaniline was used instead of N-methylaniline and 3-bromo-4, 5-dichloro-N, N-diphenylaniline was used instead of 1-bromo-2, 3-dichlorobenzene.

MS[M+H]⁺＝557

2) Synthesis of Compound 1-11-B

Compound 1-11-B was produced in the same manner as Compound 1-1-B, except that [ Compound 1-11-A ] was used in place of [ Compound 1-1-A ] and N- (4- (tert-butyl) phenyl) -3-fluoroaniline was used in place of N-methylaniline.

MS[M+H]⁺＝744

3) Synthesis of Compound 1-11-C

Compound 1-11-C was produced by the same method as Compound 1-1, except that [ Compound 1-11-B ] was used instead of [ Compound 1-1-B ].

MS[M+H]⁺＝718

4) Synthesis of Compounds 1-11

Under nitrogen atmosphere, reacting [ compound 1-11-C ]](20g) Potassium carbonate (7.7g) and Pd (PPh)₃)₄(tetrakis (triphenylphosphine) palladium (0): Tetrakis (triphenylphoshine) palladium (0)) (1.61g) was added to dimethylAcetamide (140ml) was stirred at 120 ℃ for 1 hour. The reaction solution was cooled to room temperature and then filtered. Then, the reaction mixture was purified by a silica gel short-path chromatography column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (the volume ratio of heptane/ethyl acetate ═ 1), thereby obtaining [ compound 1-11](28.0g)。

MS[M+H]⁺＝698

< production example 2: chemical formula 2>

< production example 2-1> Synthesis of Compound 2-1

1) Synthesis of Compound 2-1-A

Under a nitrogen stream, 2- ([1,1' -biphenyl)]After (4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (15g, 43.6mmol) and (3, 5-dichlorophenyl) boronic acid (9.2g, 47.9mmol) were dissolved in 150mL of a tetrahydrofuran solvent, an aqueous solution of potassium carbonate (12.1g, 87.3mmol) was added, and the mixture was stirred with heating. Under reflux, Pd (PPh) was added₃)₄(1.5g, 1.3mmol), and the mixture was stirred with heating for 6 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then the potassium carbonate solution is removed and filtered. The filtered solid was washed with ethanol, thereby producing compound 2-1-a (17.8g, yield 90%).

MS[M+H]⁺＝454

2) Synthesis of Compound 2-1-B

Compound 2-1-A (17.8g, 39.2mmol) and bis (pinacolato) diboron (10.9g, 43.1mmol) were dissolved in 180mL of bis under a nitrogen stream

After the alkane solvent was added potassium acetate (11.5g, 117.5mmol), and the mixture was stirred with heating. Under reflux, Pd (dba) is added₂(bis (dibenzylideneacetone) palladium (0): bis (dibenzylideneacetone) palladium (0)) (0.7g, 1.2mmol) and PCy₃(Tricyclohexylphosphine: Tricyclohexylphosphine) (0.7g, 2.4mmol), and stirred with heating for 8 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then impurities are removed through one-time filtration. The filtrate was added to water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was washed with ethanol to give compound 2-1-B (21g, yield 84%).

MS[M+H]⁺＝638

3) Synthesis of Compound 2-1

Compound 2-1-B (21g, 32.9mmol) and 1-bromonaphthalene (14.3g, 69.2mmol) were dissolved in tetrahydrofuran under a nitrogen stream, and then potassium carbonate (18.2g, 132.8mmol) was added as an aqueous solution, followed by heating and stirring. Under reflux, the catalyst Pd (PPh) is added₃)₄(1.2g, 1.0mmol), and the mixture was stirred under heating for 8 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then the potassium carbonate solution is removed and filtered. The solid obtained by filtration was washed with ethanol, thereby producing compound 2-1(18g, yield 85%).

MS[M+H]⁺＝638

The data on the confirmation of the synthesis of the above compound 2-1 are shown in FIG. 3.

< production example 2-2> Synthesis of Compound 2-2

After compound 2-1-B (21g, 32.9mmol) and 2-bromonaphthalene (14.3g, 69.2mmol) were dissolved in tetrahydrofuran under a nitrogen stream, potassium carbonate (18.2g, 132.8mmol) was added as an aqueous solution, and stirred with heating. Under reflux, the catalyst Pd (PPh) is added₃)₄(1.2g, 1.0mmol), and the mixture was stirred under heating for 8 hours. After the reaction is finished, the temperature is reduced to normal temperature and then removedPotassium carbonate solution and filtered. The filtered solid was washed with ethanol, thereby producing compound 2-2(18g, yield 85%).

MS[M+H]⁺＝638

The data on the confirmation of the synthesis of the above compound 2-2 are shown in FIG. 4.

< production example 2-3> Synthesis of Compound 2-3

1) Synthesis of Compound 2-3-A

Compound 2-3-a was produced in the same manner as compound 2-1-a except that (3-bromo-5-chlorophenyl) boronic acid was used instead of (3, 5-dichlorophenyl) boronic acid.

MS[M+H]⁺＝499

2) Synthesis of Compound 2-3-B

Compound 2-3-A (20g, 40.1mmol) and 1-naphthylboronic acid (7.6g, 44.1mmol) were dissolved in 1.4-bis under a nitrogen stream

After the addition of the alkyl, potassium phosphate (17.0g, 80.2mmol) was added in the form of an aqueous solution, and stirred with heating. Under reflux, the catalyst Pd (PPh) is added₃)₄(1.4g, 1.2mmol), and the mixture was stirred under heating for 8 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol, thereby producing compound 2-3-B (18g, yield 82%).

MS[M+H]⁺＝546

3) Synthesis of Compounds 2-3

Compound 2-3 was produced in the same manner as Compound 2-1, except that Compound 2-3-B was used in place of Compound 2-1-B and (4- (1-naphthyl) phenyl) boronic acid was used in place of 1-bromonaphthalene.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above-mentioned compounds 2 to 3 are shown in FIG. 5.

< production examples 2-4> Synthesis of Compounds 2-4

Compound 2-4 was produced by the same method as compound 2-3, except that (4- (2-naphthyl) phenyl) boronic acid was used instead of (4- (1-naphthyl) phenyl) boronic acid.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 4 are shown in FIG. 6.

< production examples 2-5> Synthesis of Compounds 2-5

1) Synthesis of Compound 2-5-B

Compound 2-5-B was produced in the same manner as Compound 2-3-B, except that 2-naphthylboronic acid was used instead of 1-naphthylboronic acid.

MS[M+H]⁺＝546

2) Synthesis of Compounds 2-5

Compound 2-5 was produced by the same method as compound 2-3, except that compound 2-5-B was used instead of compound 2-3-B and (4- (2-naphthyl) phenyl) boronic acid was used instead of (4- (1-naphthyl) phenyl) boronic acid.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 5 are shown in FIG. 7.

< production examples 2-6> Synthesis of Compounds 2-6

Compound 2-6 was produced by the same method as compound 2-5, except that (4- (1-naphthyl) phenyl) boronic acid was used instead of (4- (2-naphthyl) phenyl) boronic acid.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 6 are shown in FIG. 8.

< production examples 2-7> Synthesis of Compounds 2-7

Compound 2-7 was produced in the same manner as Compound 2-1, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]⁺＝738

< production examples 2-8> Synthesis of Compounds 2-8

1) Synthesis of Compound 2-8-A

Compound 2-8-a was produced in the same manner as compound 2-1-a except that 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]⁺＝454

2) Synthesis of Compound 2-8-B

Compound 2-8-B was produced by the same method as Compound 2-1-B, except that Compound 2-8-A was used instead of Compound 2-1-A.

MS[M+H]⁺＝638

3) Synthesis of Compounds 2 to 8

Compound 2-8 was produced by the same method as that for Compound 2-7, except that Compound 2-8-B was used instead of Compound 2-1-B.

MS[M+H]⁺＝738

< production examples 2-9> Synthesis of Compounds 2-9

Compounds 2 to 9 were produced in the same manner as in compound 2 to 8, except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.

MS[M+H]⁺＝638

The data on the confirmation of the synthesis of the above compounds 2 to 9 are shown in FIG. 9.

< production examples 2-10> Synthesis of Compounds 2-10

Compounds 2 to 10 were produced in the same manner as in Compound 2 to 8, except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.

MS[M+H]⁺＝638

The data on the confirmation of the synthesis of the above compounds 2 to 10 are shown in FIG. 10.

< production examples 2-11> Synthesis of Compounds 2-11

1) Synthesis of Compound 2-11-A

Compound 2-11-a was produced in the same manner as compound 2-3-a except that 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]⁺＝499

2) Synthesis of Compound 2-11-B

Compound 2-11-B was produced in the same manner as Compound 2-3-B, except that 2-11-A was used instead of Compound 2-3-A.

MS[M+H]⁺＝546

3) Synthesis of Compounds 2-11

Compound 2-11 was produced by the same method as Compound 2-3, except that Compound 2-11-B was used instead of Compound 2-3-B.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 11 are shown in FIG. 11.

< production examples 2-12> Synthesis of Compounds 2-12

Compound 2-12 was produced by the same method as that for Compound 2-4, except that Compound 2-11-B was used instead of Compound 2-3-B.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 12 are shown in FIG. 12.

< production examples 2-13> Synthesis of Compounds 2-13

1) Synthesis of Compound 2-13-B

Compound 2-13-B was produced by the same method as Compound 2-5-B, except that Compound 2-11-A was used instead of Compound 2-3-A.

MS[M+H]⁺＝546

2) Synthesis of Compounds 2-13

Compound 2-13 was produced by the same method as Compound 2-5 except that Compound 2-13-B was used instead of Compound 2-5-B.

MS[M+H]⁺＝714

The data on the confirmation of the synthesis of the above compounds 2 to 13 are shown in FIG. 13.

< production examples 2-14> Synthesis of Compounds 2-14

Compound 2-14 was produced by the same method as compound 2-13, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS[M+H]⁺＝714

< production examples 2-16> Synthesis of Compounds 2-16

1) Synthesis of Compound 2-16-A

Compound 2-16-a was produced in the same manner as compound 2-1-a except that 2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]⁺＝468

2) Synthesis of Compound 2-16-B

Compound 2-16-B was produced by the same method as Compound 2-1-B, except that Compound 2-16-A was used instead of Compound 2-1-A.

MS[M+H]⁺＝652

3) Synthesis of Compounds 2-16

Compound 2-16 was produced by the same method as Compound 2-1, except that Compound 2-16-B was used instead of Compound 2-1-B.

MS[M+H]⁺＝652

The data on the confirmation of the synthesis of the above compounds 2 to 16 are shown in FIG. 14.

< production examples 2-17> Synthesis of Compounds 2-17

Compound 2-17 was produced in the same manner as Compound 2-1, except that Compound 2-16-B was used in place of Compound 2-1-B and 2-bromonaphthalene was used in place of 1-bromonaphthalene.

MS[M+H]⁺＝652

The data on the confirmation of the synthesis of the above compounds 2 to 17 are shown in FIG. 15.

< production examples 2-18> Synthesis of Compounds 2-18

1) Synthesis of Compound 2-18-A

Compound 2-18-a was produced in the same manner as compound 2-3-a except that 2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]⁺＝512

2) Synthesis of Compound 2-18-B

Compound 2-18-B was produced by the same method as Compound 2-3-B, except that Compound 2-18-A was used instead of Compound 2-3-A.

MS[M+H]⁺＝560

3) Synthesis of Compounds 2-18

Compound 2-18 was produced by the same method as Compound 2-3, except that Compound 2-18-B was used instead of Compound 2-3-B.

MS[M+H]⁺＝728

< production examples 2-19> Synthesis of Compounds 2-19

Compounds 2 to 19 were produced in the same manner as in Compound 2 to 4, except that Compound 2-18-B was used in place of Compound 2-3-B.

MS[M+H]⁺＝728

< production examples 2-20> Synthesis of Compounds 2-20

1) Synthesis of Compound 2-20-B

Compound 2-20-B was produced in the same manner as Compound 2-18-B, except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid.

MS[M+H]⁺＝560

2) Synthesis of Compounds 2-20

Compound 2-20 was produced by the same method as Compound 2-5 except that Compound 2-20-B was used instead of Compound 2-5-B.

MS[M+H]⁺＝728

The data on the confirmation of the synthesis of the above compounds 2 to 20 are shown in FIG. 16.

< production examples 2-21> Synthesis of Compounds 2-21

Compound 2-21 was produced by the same method as compound 2-20, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS[M+H]⁺＝728

< production examples 2-22> Synthesis of Compounds 2-22

Compounds 2 to 22 were produced in the same manner as in compound 2 to 16, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]⁺＝752

The data on the confirmation of the synthesis of the above compounds 2 to 22 are shown in FIG. 17.

< production examples 2-23> Synthesis of Compounds 2-23

1) Synthesis of Compound 2-23-A

Compound 2-23-a was produced in the same manner as compound 2-1-a except that (2, 5-dichlorophenyl) boronic acid was used instead of (3, 5-dichlorophenyl) boronic acid.

MS[M+H]⁺＝454

2) Synthesis of Compound 2-23-B

Compound 2-23-B was produced by the same method as Compound 2-1-B, except that Compound 2-23-A was used instead of Compound 2-1-A.

MS[M+H]⁺＝638

3) Synthesis of Compounds 2-23

Compound 2-23 was produced by the same method as Compound 2-1, except that Compound 2-23-B was used instead of Compound 2-1-B.

MS[M+H]⁺＝638

< production examples 2-24> Synthesis of Compounds 2-24

Compounds 2-24 were produced in the same manner as in compound 2-23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS[M+H]⁺＝638

< production examples 2-25> Synthesis of Compounds 2-25

Compounds 2 to 25 were produced in the same manner as in compound 2 to 23, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]⁺＝738

< production examples 2-26> Synthesis of Compounds 2-26

1) Synthesis of Compound 2-26-A

Compound 2-26-a was produced in the same manner as compound 2-3-a except that 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine and (2-bromo-4-chlorophenyl) boronic acid was used instead of (3-bromo-5-chlorophenyl) boronic acid.

MS[M+H]⁺＝472

2) Synthesis of Compound 2-26-B

Compound 2-26-B was produced by the same method as Compound 2-3-B, except that Compound 2-26-A was used instead of Compound 2-3-A.

MS[M+H]⁺＝520

3) Synthesis of Compounds 2-26

Compound 2-26 was produced in the same manner as compound 2-3, except that compound 2-26-B was used instead of compound 2-3-B and (4- (phenanthren-9-yl) phenyl) boronic acid was used instead of (4- (naphthalen-1-yl) phenyl) boronic acid.

MS[M+H]⁺＝738

[ examples ]

< examples 1 to 1>

A glass substrate (corning 7059 glass) on which ITO (indium tin oxide) was coated in a thickness of 100nm was placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water used was distilled water obtained by twice filtering with a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.

On the ITO transparent electrode thus prepared, hexacyanoferrazine (HAT-CN) was thermally vacuum-evaporated to form a hole injection layer having a thickness of 50 nm.

On the hole injection layer, a compound HT1, which is a substance that transports holes, was vacuum-evaporated to form a hole transport layer having a thickness of 40 nm.

On the hole transport layer, H1 and compound 1-1 were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer having a thickness of 30 nm.

On the light-emitting layer, compound ET1 was vacuum-deposited to form an electron control layer having a thickness of 3 nm.

On the electron control layer, an electron injection and transport layer having a thickness of 35nm was formed by vacuum evaporation of the compound 2-1 and the compound LiQ (8-quinolinolato) at a weight ratio of 1: 1.

On the above electron injection and transport layer, lithium fluoride (LiF) and aluminum were sequentially evaporated at thicknesses of 1.2nm and 200nm to form a cathode, thereby fabricating an organic light emitting device.

In the above process, the deposition rate of organic substance is maintained at 0.04 nm/s to 0.07 nm/s, the deposition rate of lithium fluoride is maintained at 0.03 nm/s, the deposition rate of aluminum is maintained at 0.2 nm/s, and the degree of vacuum is maintained at 2X 10 during deposition^-7Hold in the palm to 5 x 10^-6And (4) supporting.

< examples 1-2 to 1-17>

Organic light-emitting devices were produced in the same manner as in example 1-1 above, except that compounds of table 1 below were used instead of compound 1-1 and compound 2-1, respectively.

< comparative examples 1-1 to 1-17>

For the organic light emitting devices of examples and comparative examples, respectively, at 10mA/cm²The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm²The time required for the luminance to become 98% with respect to the initial luminance was measured at the current density of (LT 98). The results are shown in table 1 below.

[ Table 1]

Claims

1. An organic light emitting device, comprising:

an anode;

a cathode provided to face the anode;

a light-emitting layer which is provided between the anode and the cathode and contains a compound represented by the following chemical formula 1;

a hole transport region provided between the anode and the light-emitting layer; and

an electron transport region which is provided between the cathode and the light-emitting layer and contains a compound represented by the following chemical formula 2:

chemical formula 1

In the chemical formula 1, the first and second,

A. b and C are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

x1 and X2 are each independently O, CR1R2 or NR3,

r1 to R3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

adjacent groups of R1 to R3, A, B and C are optionally bonded to each other to form a substituted or unsubstituted ring,

chemical formula 2

In the chemical formula 2, the first and second organic solvents,

two or more of X4 to X6 are N, and the remainder are CH,

ar1 and Ar2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l is a substituted or unsubstituted 3-valent aryl group, or a substituted or unsubstituted 3-valent heterocyclic group,

y is a substituted or unsubstituted polycyclic aromatic group,

n is 2, and

when n is 2, 2Y's are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1:

chemical formula 1-1

In the chemical formula 1-1,

A. b and C are as defined in claim 1,

r 'and R' are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and

adjacent groups of R', R ", A, B, and C are optionally bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

3. The organic light emitting device according to claim 1, wherein the chemical formula 1 is selected from the following structural formulae:

4. the compound of claim 1, wherein the chemical formula 2 is a compound selected from the following structural formulae:

5. the organic light emitting device according to claim 1, wherein the light emitting layer comprises a host and contains the dopant of chemical formula 1.

6. The organic light emitting device of claim 5, wherein a weight ratio of the host to the dopant is 90:10 to 99: 1.

7. The organic light emitting device according to claim 5, wherein the host comprises a compound represented by the following chemical formula 4:

chemical formula 4

In the chemical formula 4, the first and second organic solvents,

l101 and L102 are the same as or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

r101 to R108 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,

m1 and m2 are each an integer of 0 to 5,

when m1 is 2 or more, L101 s are the same as or different from each other, and

when m2 is 2 or more, L102 s may be the same as or different from each other.

8. The organic light emitting device according to claim 1, wherein the electron transport region comprises an electron regulation layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron regulation layer, the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound represented by chemical formula 2.