CN113727980A

CN113727980A - Compound and organic light emitting device including the same

Info

Publication number: CN113727980A
Application number: CN202080030276.8A
Authority: CN
Inventors: 河宰承; 许瀞午; 许东旭; 金性昭; 千民承; 曹惠慜
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-07-05
Filing date: 2020-07-01
Publication date: 2021-11-30
Also published as: KR20210004860A; WO2021006532A1; KR102445078B1

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device including the same

Technical Field

The specification claims priority of korean patent application No. 10-2019-0081380, filed on 5.7.2019 from the korean patent office, the entire contents of which are incorporated herein.

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

Background

An organic light-emitting device is a light-emitting device using an organic semiconductor substance, and requires communication of holes and/or electrons between an electrode and the organic semiconductor substance. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first type is a light emitting device in a form in which an exciton (exiton) is formed in an organic layer by a photon flowing into the device from an external light source, the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with an electrode by applying a voltage or current to 2 or more electrodes, and the light-emitting device operates by the injected electrons and holes.

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 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 adjusting layer, a hole adjusting 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. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron inhibiting substances, electron transport materials, electron injection materials, and the like, according to functions. The light-emitting materials include blue, green, and red light-emitting materials, and yellow and orange light-emitting materials required for realizing a more natural color, depending on the light-emitting color.

In addition, for the purpose of an increase in color purity and an increase in luminous efficiency based on energy transfer, as a light emitting material, a host/dopant system may be used. The principle is that when a small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. In this case, since the wavelength of the host is shifted to the wavelength range of the dopant, light having a desired wavelength can be obtained according to the kind of the dopant used.

In order to fully utilize the excellent characteristics of the organic light emitting device, the materials constituting the organic layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron suppressing material, an electron transporting material, and an electron injecting material, are stable and effective, and therefore, development of new materials is continuously required.

Disclosure of Invention

Technical subject

The present specification provides compounds and organic light emitting devices comprising the same.

Means for solving the problems

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

x1 is O or S,

l1 to L3 are each independently a direct bond, a substituted or unsubstituted cycloalkyl group having a valency of 2, a substituted or unsubstituted aryl group having a valency of 2, or a substituted or unsubstituted heteroaryl group having a valency of 2,

ar1 and Ar2 are each independently substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

ar3 is hydrogen, a nitrile 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, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted heteroaryl group containing 1 or more of O and S as a heteroatom,

a to c are each independently an integer of 1 to 4,

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

In addition, the present specification provides an organic light emitting device, including: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

Effects of the invention

Compounds according to one embodiment of the present specification are prepared by

Diazoles or thiadiazoles with pyrimidinesThe pyridine is structurally bound to regulate electron affinity, thereby improving electron transport ability. Therefore, when the organic light emitting device is used as an electron adjusting layer, an electron transporting layer and/or a host, the organic light emitting device has the effects of improving the brightness of the device, reducing the driving voltage, improving the light emitting efficiency and improving the life characteristics.

Drawings

Fig. 1 illustrates an example of an organic light emitting device according to an embodiment of the present specification.

< description of symbols >

1: a first electrode

2: hole injection layer

3: hole transport layer

4: hole-regulating layer

5: luminescent layer

6: electronically regulated layer

7: electron transport layer

8: electron injection layer

9: a second electrode.

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

x1 is O or S,

a to c are each independently an integer of 1 to 4,

The compound represented by the above chemical formula 1 is prepared by including pyrimidine together with

The structure of the oxadiazole or the thiadiazole has an effect of adjusting electron affinity to improve electron transport ability. In particular, the above

The substitution of oxadiazole or thiadiazole at the L3 position in chemical formula 1, which results in the combination of asymmetric structures of azines when compared with the L2 position, has an advantage that the electron transport properties can be adjusted by increasing the intramolecular polarity.

In the present specification, examples of the substituent are described below, but the substituent is 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 with 1 or 2 or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, an amino group, a phosphine oxide group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an alkylthio group, an aryl group, a sulfonyl group, and a heterocyclic group, or 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 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-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 2-ethylpentyl group, 2-ethylpropyl group, 1-ethylpropyl group, 2-ethylpentyl group, 2-pentyl group, and the like, 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 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 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 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.

In the present specification, the above alkylthio group may be straight, branched or cyclic. The number of carbon atoms of the alkylthio group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, there are methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio and p-methylbenzylthio, etc., but not limited thereto.

In the present specification, the number of carbon atoms of the above-mentioned aryl group is not particularly limited, but may be 6 to 60 or 6 to 30, and the above-mentioned aryl group may be monocyclic or polycyclic.

In the present specification, when the aryl group is a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the above-mentioned aryl group is a polycyclic aryl group, it 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 2-valent aryl group is a 2-valent group, and may be selected from the above-mentioned examples of aryl groups, in addition to the 2-valent group.

In the present specification, the heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, Si, S, and the like. The number of carbon atoms of the heteroaryl group is not particularly limited, but it is preferable that the number of carbon atoms is 2 to 60 or 2 to 30. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, azaPyridyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiololyl, dibenzothiazolyl, phenanthrolinyl (phenanthrolyl group), isoquinoyl

Azolyl, thiadiazolyl, phenothiazinyl, phenoxazine

Oxazine groups and their fused structures, and the like, but are not limited thereto.

In the present specification, the 2-valent heteroaryl group is a 2-valent group, and may be selected from the above-mentioned examples of the heteroaryl group.

In the present specification, the above-mentioned cycloalkyl group having a valence of 2 is a group having a valence of 2, and may be selected from the above-mentioned examples of cycloalkyl groups.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amino group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, naphthylamino group, biphenylamino group, anthrylamino group, 9-methyl-anthrylamino group, diphenylamino group, phenylnaphthylamino group, ditolylamino group, phenyltolylamino group, and triphenylamino group.

In the present specification, the number of carbon atoms of the imide group, the carbonyl group, and the ester group is not particularly limited, but is preferably 1 to 50.

In the present specification, in the amide group, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

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 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, the silyl group is a substituent containing Si and the above-mentioned Si atom is directly linked as a radical, represented by-SiR₁₀₄R₁₀₅R₁₀₆Is represented by R₁₀₄To R₁₀₆The substituents may be each independently at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group, which may be the same or different from each other. 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 ring means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring or a fused ring of an aromatic ring and an aliphatic ring, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the hydrocarbon ring has a valence of 1.

In the present specification, the aromatic ring may be a monocyclic ring or a polycyclic ring, and may be selected from the above-mentioned illustrations of aryl groups, except that it is not 1-valent.

In the present specification, the heterocyclic ring 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, Si, S, and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from the heteroaryl groups exemplified above except that it has a valence of 1.

In one embodiment of the present specification, X1 is S.

In one embodiment of the present specification, X1 is O.

In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In the above chemical formulas 1-1 to 1-4,

l1 to L3, Ar1 to Ar3 and a to c are the same as defined in the above chemical formula 1.

In one embodiment of the present specification, L3 represents a direct bond, substituted or unsubstituted C₆-C₃₀Or a substituted or unsubstituted C₂-C₁₅The heteroarylene of (a), said substituent being selected from deuterium; c₁-C₁₀Alkyl groups of (a); c₆-C₃₀Aryl of (a); and C comprising more than one of N, O and S₂-C₃₀The heteroaryl group of (1) or 2 or more substituents and/or 2 or more substituents among the above-exemplified substituents may be unsubstituted or substituted by a substituent.

According to one embodiment of the present disclosure, L3 represents a direct bond, a substituted or unsubstituted 2-valent phenyl group, a substituted or unsubstituted 2-valent biphenyl group, a substituted or unsubstituted 2-valent terphenyl group, a substituted or unsubstituted 2-valent naphthyl group, a substituted or unsubstituted 2-valent anthryl group, a substituted or unsubstituted 2-valent fluorenyl group, a substituted or unsubstituted 2-valent phenanthryl group, a substituted or unsubstituted 2-valent triphenylene group, a substituted or unsubstituted 2-valent cyclohexyl group, or a substituted or unsubstituted 2-valent dibenzo-bis (dibenzo-bis) group

An alkyl group, a substituted or unsubstituted carbazolyl group having a valence of 2, a substituted or unsubstituted furyl group having a valence of 2, a substituted or unsubstituted dibenzofuryl group having a valence of 2, a substituted or unsubstituted dibenzothienyl group having a valence of 2, or a substituted or unsubstituted benzo group having a valence of 2

(iii) oxazolyl, said substituent being selected from deuterium; c₁-C₁₀Alkyl groups of (a); c₆-C₃₀Aryl of (a); and C comprising more than one of N, O and S₂-C₃₀The heteroaryl group of (1) or 2 or more substituents and/or 2 or more substituents among the above-exemplified substituents may be unsubstituted or substituted by a substituent.

According to another embodiment, the above L3 is a direct bond, a substituted or unsubstituted 2-valent phenyl group, a substituted or unsubstituted 2-valent biphenyl group, a substituted or unsubstituted 2-valent terphenyl group, a substituted or unsubstituted 2-valent naphthyl group, a substituted or unsubstituted 2-valent anthryl group, a substituted or unsubstituted 2-valent fluorenyl group, a substituted or unsubstituted 2-valent phenanthryl group, a substituted or unsubstituted 2-valent triphenylene groupCyclohexyl, substituted or unsubstituted 2-valent dibenzo bis

According to another embodiment, the above L3 represents a direct bond, a substituted or unsubstituted 2-valent phenyl group, a substituted or unsubstituted 2-valent biphenyl group, a substituted or unsubstituted 2-valent terphenyl group, a substituted or unsubstituted 2-valent naphthyl group, a substituted or unsubstituted 2-valent anthryl group, a substituted or unsubstituted 2-valent fluorenyl group, a substituted or unsubstituted 2-valent phenanthryl group, a substituted or unsubstituted 2-valent triphenylene group, a substituted or unsubstituted 2-valent cyclohexyl group, a substituted or unsubstituted 2-valent dibenzo-bis (biphenyl-bis) group

Azolyl radical, the substituents being chosen from deuterium, methyl, phenyl, naphthyl, benzo

Azolyl, phenylbenzofuranyl, and phenyleneyl groups

Phenyl, phenyl substituted by oxadiazolyl

Oxadiazolyl and naphthyl

1 or more substituents in the oxadiazolyl group are substituted or unsubstituted.

According to an embodiment of the present disclosure, when c is an integer of 1 to 4 and c is 2 or more, 2 or more L3 may be the same or different from each other.

In one embodiment of the present specification, L3 may be represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

q1 to Q3 are each independently NR, CR 'R', O or S,

r1 to R5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r, R 'and R' are each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, R 'and R' may combine with each other to form a ring,

d2 is an integer from 0 to 2,

d3 is an integer from 0 to 3,

d4 is an integer from 0 to 4,

d5 is an integer from 0 to 5,

d6 is an integer from 0 to 6,

d7 is an integer from 0 to 7,

d1 is an integer from 1 to 4,

d is 1 or 2, and the compound has the structure of,

and (c) is a position linked to the above chemical formula 1.

In one embodiment of the present specification, Q1 and Q2 are each O.

In one embodiment of the present specification, Q3 is NR, CR' R ", O or S.

In one embodiment of the present specification, R1 to R5 are each independently hydrogen, deuterium, or C₁-C₁₀Alkyl of (C)₆-C₃₀Or a heteroaryl group containing one or more of O and S.

In one embodiment of the present specification, R1 to R5 are each independently hydrogen, deuterium, methyl, phenyl, naphthyl, benzo

Oxazolyl, benzothiazolyl, benzothienyl, or benzofuranyl.

In one embodiment of the present specification, R, R' and R "are each independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀The above R 'and R' may combine with each other to form a cycloalkyl or aryl group.

In one embodiment of the present specification, R, R 'and R "are each independently hydrogen, methyl, or phenyl, and R' and R" may combine with each other to form a fluorenyl group.

In one embodiment of the present specification, d1 is 1 to 3.

In one embodiment of the present specification, d1 is 1 or 2.

In one embodiment of the present specification, d1 is 1.

In one embodiment of the present specification, d is 1.

In one embodiment of the present specification, Ar1 and Ar2 are each independently substituted or unsubstituted C₆-C₃₀Aryl of (2), or substituted or unsubstituted C₂-C₃₀The heteroaryl group of (a).

According to another embodiment, each of Ar1 and Ar2 described above is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group, said substituents being selected from deuterium, a nitrile group, a halogen group, C₁-C₁₀Alkyl of (C)₁-C₁₀Alkoxy group of (A), and C₆-C₃₀The aryl group of (1) or (2) or more substituents and/or the substituents formed by connecting 2 or more substituents among the above-exemplified substituents are substituted or unsubstituted.

According to another embodiment, each of Ar1 and Ar2 described above is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group, which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, a methyl group, a trifluoromethoxy group, and a phenyl group.

In one embodiment of the present specification, Ar1 and Ar2 may each be represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

q4 is each independently NRa, CRbRc, O or S,

r6 and R7 are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

ra, Rb and Rc are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and Rb and Rc may be bonded to each other to form a ring,

d4 is an integer from 0 to 4,

d5 is an integer from 0 to 5,

d7 is an integer from 0 to 7,

d8 is an integer from 0 to 8,

d9 is an integer from 0 to 9,

e is an integer of 1 to 3,

and (c) is a position linked to the above chemical formula 1.

In one embodiment of the present specification, R6 and R7 are each independently hydrogen, deuterium, or C₁-C₁₀Alkyl of (C)₆-C₃₀Or a heteroaryl group containing one or more of O and S.

In one embodiment of the present specification, R6 and R7 are each independently hydrogen, deuterium, methyl, phenyl, nitrile, fluoromethoxy, or naphthyl.

In one embodiment of the present specification, Ra, Rb and Rc are each independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀The above Rb and Rc may combine with each other to form a cycloalkyl group or an aryl group.

In one embodiment of the present specification, Ra, Rb and Rc are each independently hydrogen, methyl or phenyl, and Rb and Rc may be combined with each other to form a fluorenyl group.

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

In one embodiment of the present specification, e is 1.

According to an embodiment of the present specification, Ar3 represents hydrogen, a nitrile group, or a substituted or unsubstituted C₃-C₂₀Trialkylsilyl group, substituted or unsubstituted C₁₈-C₃₀Triarylsilyl group of (C), substituted or unsubstituted₁-C₂₀Alkyl, substituted or unsubstituted C₃-C₂₀Cycloalkyl, substituted or unsubstitutedC of (A)₆-C₃₀Or a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted C group containing 1 or more of O and S as a hetero atom₂-C₃₀The heteroaryl group of (a).

When the compound in which Ar3 is a monocyclic N-containing heteroaryl group such as pyridine or pyrimidine is used for a device, the device balance is broken, and the energy level of the adjacent layer is not matched, whereby the efficiency and lifetime of the device are reduced.

In one embodiment of the present specification, Ar3 represents hydrogen, a nitrile group, a linear or branched alkyl group, a monocyclic cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.

According to another embodiment, Ar3 described above is hydrogen, a nitrile group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted carbazolyl group. The above substituents being selected from deuterium, nitrile group, C₁-C₁₀Alkyl of (C)₃-C₂₀Trialkylsilyl group of (1), C₁₈-C₃₀Triarylsilyl group of (C)₆-C₃₀OfRadical and C₂-C₃₀The heteroaryl group of (1) or 2 or more substituents and/or 2 or more substituents among the above-exemplified substituents may be unsubstituted or substituted by a substituent.

According to another embodiment, Ar3 described above is hydrogen, a nitrile group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted carbazolyl group. The above-mentioned substituent is unsubstituted or substituted with 1 or more substituents selected from deuterium, nitrile group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, triphenylsilyl group, phenyl group, naphthyl group, phenylnaphthyl group, phenanthryl group, carbazolyl group, dibenzofuranyl group and phenyldibenzofuranyl group.

In one embodiment of the present specification, each of L1 and L2 independently represents a direct bond, a substituted or unsubstituted C₆-C₃₀Aryl group having a valence of 2, or substituted or unsubstituted C₂-C₃₀A heteroaryl group having a valence of 2.

According to another embodiment, each of L1 and L2 described above is independently a direct bond, a substituted or unsubstituted 2-valent phenyl group, a substituted or unsubstituted 2-valent biphenyl group, a substituted or unsubstituted 2-valent terphenyl group, a substituted or unsubstituted 2-valent anthracenyl group, or a substituted or unsubstituted 2-valent dibenzofuranyl group.

According to another embodiment, a and b are each 0 or 1.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 may be any one selected from the following structural formulae.

The compound according to one embodiment of the present specification can be produced by a production method described later.

For example, the compound of chemical formula 1 can be produced according to the production examples described below, substituents can be bonded by a method known in the art, and the type, position, or number of substituents can be changed according to a technique known in the art.

In the present specification, "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as an absolute value representing the energy value. For example, the energy level depth means that the absolute value increases in the negative direction from the vacuum level.

In the present specification, HOMO (highest occupied molecular orbital) refers to a molecular orbital function (highest occupied molecular orbital) of a region with the highest energy in which an electron is located in a region that can participate in binding, LUMO (lowest unoccupied molecular orbital) refers to a molecular orbital function (lowest unoccupied molecular orbital) of a region with the lowest energy in which an electron is located in an anti-binding region, and HOMO level refers to a distance from a vacuum level to HOMO. Further, the LUMO level refers to the distance from the vacuum level to the LUMO.

In the present specification, a bandgap (bandgap) refers to a difference in energy levels of HOMO and LUMO, that is, a HOMO-LUMO energy Gap (Gap).

In addition, the present specification provides an organic light emitting device comprising the above-mentioned compound.

An embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

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

The organic layer of the organic light-emitting device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a hole adjusting layer, a light emitting layer, an electron adjusting 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 specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound. Specifically, the light-emitting layer contains a host and a dopant, and the compound is contained as a host.

In one embodiment of the present disclosure, the light-emitting layer is a red light-emitting layer or a green light-emitting layer.

In one embodiment of the present specification, as the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, perylene, and the like having an arylamine group,

Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

In one embodiment of the present specification, when the compound is contained in a host of a light-emitting layer, a dopant is a metal complex, preferably an iridium complex.

In one embodiment of the present specification, the dopant may be selected from the following structural formulae, but is not limited thereto.

In one embodiment of the present disclosure, the organic layer includes 1 or more electron transport layers, and at least one of the electron transport layers includes the compound.

According to another embodiment, the electron transport layer comprising the above compound further comprises an organometallic complex.

In one embodiment of the present disclosure, the organic layer includes a light-emitting layer and an electron-transporting layer, and the light-emitting layer and the electron-transporting layer include the compound.

In one embodiment of the present specification, the organic layer includes 1 or more electron-modulating layers, and at least one of the electron-modulating layers includes the compound.

In one embodiment of the present disclosure, the organic layer includes an electron control layer and an electron transport layer, and the electron control layer and the electron transport layer include the compound.

According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer may include the compound in an amount of 5 wt% to 99 wt%, preferably 10 wt% to 30 wt%, based on 100 wt% of the light emitting layer.

In one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer and also includes a dopant. At this time, the content of the above dopant may be 10 to 99 wt%, preferably, 10 to 50 wt%, based on 100 wt% of the host.

According to one embodiment of the present disclosure, when the light-emitting layer includes 2 kinds of hosts, a mass ratio of the 2 kinds of hosts is 1:9 to 9: 1.

When the compound represented by chemical formula 1 of the present specification is used as a host of a light emitting layer, the lifetime and efficiency of a device are improved.

According to an embodiment of the present disclosure, the organic layer includes an electron transport layer, and the electron transport layer may include the compound in an amount of 5 wt% to 99 wt%, preferably 10 wt% to 30 wt%, based on 100 wt% of the electron transport layer.

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 shows an example of the 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 first electrode 1, a hole injection layer 2, a hole transport layer 3, a hole adjusting layer 4, a light emitting layer 5, an electron adjusting layer 6, an electron transport layer 7, an electron injection layer 8, and a second electrode 9 are sequentially stacked. In the structure described above, the above-described compound may be contained in one or more layers among the above-described hole injection layer 2, hole transport layer 3, hole regulation layer 4, light-emitting layer 5, electron regulation layer 6, electron transport layer 7, and electron injection layer 8, and specifically, may be contained in the electron transport layer and/or the light-emitting layer.

The organic light-emitting device in this specification may have a structure in which a first electrode, a hole injection layer, a hole transport layer, a hole adjustment layer, a light-emitting layer, an electron adjustment layer, an electron transport layer, an electron injection layer, a second electrode, and a cover layer are sequentially stacked, but is not limited thereto.

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

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

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating 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 one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.

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

The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic layer.

The cathode is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance in order to easily inject electrons 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.

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 LiO₂Multi-layer structure material such as AlBut is not limited thereto.

The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injecting substance is a substance that can inject holes from the anode well at a low voltage, and 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, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection property can be prevented from being lowered, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of holes when the thickness of the hole injection layer is too large.

The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring 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 hole control layer may be provided between the hole transport layer and the light-emitting layer, and may be configured to effectively transfer holes from the hole transport layer, thereby controlling hole mobility and thus adjusting the amount of holes transferred to the light-emitting layer. Further, it can also function as an electron barrier that prevents electrons supplied from the light-emitting layer from being transferred to the hole transport layer. Thereby, the balance of holes and electrons in the light emitting layer is maximized, so that the light emitting efficiency can be increased, and the stability and the lifetime can be improved. As the material of the hole adjusting layer, a material known in the art can be used.

As the host material of the light-emitting layer, there is aromatic compounds in addition to the above compoundsGroup fused ring derivatives or heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

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

The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; 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.

When the light-emitting layer emits red light, as a light-emitting dopant, piqir (bis (1-phenylisoquinoline) iridium acetylacetonate, bis (1-phenylisoquinoline) acetylacetylateeridi um), PQIr (acac) (bis (1-phenylquinoline) iridium acetylacetonate, bis (1-phenylquinoline) iridium acetate, PQIr (tris (1-phenylquinoline) iridium, PtOEP (platinum octaethylporphyrin, octaethylporphyrin) and other phosphorescent materials, or Alq may be used₃(tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) aluminum) and other fluorescent substances, but the present invention is not limited thereto. When the light-emitting layer emits green light, it is operatedFor the light-emitting dopant, Ir (ppy)₃Examples of the phosphorescent substance include phosphorescent substances such as tris (2-phenylpyridine) iridium (fac tris (2-phenylpyridine)) iridi um, and fluorescent substances such as Alq3 (tris (8-hydroxyquinoline) aluminum, tris (8-hydroxyquinoline) aluminum), anthracene compounds, pyrene compounds, and boron compounds, but are not limited thereto. When the light-emitting layer emits blue light, (4, 6-F) may be used as the light-emitting dopant₂ppy)₂Examples of the fluorescent substance include phosphorescent substances such as Irpic, spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds, but are not limited thereto.

The electron adjusting layer may be provided between the light emitting layer and the electron transporting layer, and may effectively transfer electrons from the electron transporting layer to adjust electron mobility, thereby adjusting the amount of electrons transferred to the light emitting layer. Further, the hole blocking layer may also function as a hole blocking layer for preventing holes supplied from the light-emitting layer from being transferred to the electron transport layer. Thereby, the balance of holes and electrons in the light emitting layer is maximized, so that the light emitting efficiency can be increased, and the stability and the lifetime can be improved. As the material of the electron adjusting layer, a material known in the art may be used in addition to the above-described compound.

The electron transport layer can play a role in smoothly transporting electrons. The electron transport material is a material capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. In addition to the above compounds, as specific examples, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto.

In one embodiment of the present specification, the electron transport layer may further include an organometallic complex, and the organometallic complex may be mixed with the compound and included in one layer. Specifically, the compound and the organometallic complex may be mixed and then vacuum-evaporated or separately evaporated to form a mixtureAnd a lamination layer. In this case, the energy level of the organic material and the cathode or the electron injection layer can be adjusted, and the interfacial bonding ability between the organic material and the metal can be improved. As the above organometallic complex, one selected from the group consisting of LiQ, NaQ, LiF, CsF, BaF, BaO and Al can be used₂O₃But not limited thereto.

The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the electron transport property can be prevented from being lowered, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of electrons when the thickness of the electron transport layer is too thick.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: 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.

The cathode may have a coating layer thereon. As the cover layer, a material known in the art, such as a carbazole-based compound, can be used.

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 organic light emitting device according to the present specification 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

Hereinafter, in order to specifically explain the present specification, the detailed description will be given by referring to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.

< production example >

Production example 1 production of intermediates S1 to S17 and P1 to P6

After adding SM1(1 equivalent) and SM2(1.02 equivalent) to an excess of tetrahydrofuran in accordance with the combination described in table 1 below, a 2M aqueous solution of potassium carbonate (30 vol% with respect to THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was stirred under heating for 10 hours. The temperature is reduced to normal temperature, after the reaction is finished, the potassium carbonate aqueous solution is removed, and the layer is separated. After the solvent was removed, vacuum distillation was performed, and recrystallization was performed using ethyl acetate and hexane, as shown in the following table 1, to obtain S1 to S17 and P1 to P6 as products.

[ Table 1]

Production example 2 production of intermediates S1-1 and S1-2

S8 prepared in preparation example 1 was dissolved in chloroform, and after the temperature was stabilized at 0 ℃, N-bromosuccinimide (NBS) (1.01 equiv.) was added. After the temperature was stabilized to normal temperature, completion of the reaction was confirmed, and water was added and then filtered. Then, it was recrystallized from chloroform and ethyl acetate, thereby producing intermediate S1-1 of the following table 2.

In addition, an intermediate S1-2 of table 2 below was produced by the same procedure as the production procedure of S1-1, except that P6 produced in production example 1 was used instead of S8.

[ Table 2]

Production example 3 production of intermediates A1 to A4

2,4, 6-trichloropyrimidine (SM1) (1 equivalent) and SM2(1.02 equivalent) were added to an excess of tetrahydrofuran in combination as shown in Table 3 below, and then 2M aqueous potassium carbonate (30 vol% relative to THF) was added to the mixture, and tetrakis (triphenylphosphine) palladium (2 mol%) was added thereto, followed by stirring with heating for 10 hours. The temperature is reduced to normal temperature, after the reaction is finished, the potassium carbonate aqueous solution is removed, and the layer is separated. After the solvent was removed, vacuum distillation was performed, and recrystallization was performed using ethyl acetate and hexane, thereby producing a1 to a4 of table 3 below.

[ Table 3]

Production example 4 production of intermediates B1 to B10

Intermediates B1 to B10 described in the following table 4 were produced by the same procedure as in the above production example 3, except that the combination of SM1 and SM2 was replaced with the combination described in the following table 4.

[ Table 4]

PREPARATION EXAMPLE 5 preparation of intermediates C1 to C5

Intermediates C1 to C5 described in the following table 5 were produced by the same procedure as in the above production example 3, except that the combination of SM1 and SM2 was replaced with the combination described in the following table 5.

[ Table 5]

Production example 6 production of intermediates D1 to D14

SM1(1 am) was prepared according to the combination shown in Table 6 belowAmount) and SM2(1.3 equiv.) into 1, 4-bis

To an alkane (12 times the amount of SM1 based on the mass ratio), potassium acetate (3 equivalents) was added, and the mixture was stirred and refluxed. Then, palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) were added to 1, 4-bis

After stirring in an alkane for 5 minutes, the mixture was poured in, and after 2 hours, the reaction was confirmed to be complete, and the mixture was cooled to room temperature. Then, ethanol and water were charged, filtered, and recrystallized from ethyl acetate, thereby producing D1 to D14 of table 6 below.

[ Table 6]

Production example 7 production of intermediate E1

Intermediate E1 described in table 7 below was produced by the same procedure as in production example 3 above, except that the combination of SM1 and SM2 was replaced with the combination described in table 7 below.

[ Table 7]

Production example 8 production of intermediate F1

Intermediate F1 described in table 8 below was produced by the same procedure as in production example 6 above, except that the combination of SM1 and SM2 was replaced with the combination described in table 8 below.

[ Table 8]

PREPARATION EXAMPLE 9 preparation of Compounds 1 to 28

Compounds 1 to 28 shown in table 9 below were produced by the same procedure as in production example 3, except that the combination of SM1(1 equivalent) and SM2(1.05 equivalent) was replaced with the combination shown in table 9 below.

[ Table 9]

PREPARATION EXAMPLE 10 preparation of Compounds 29 and 30

(1) Production of Compound 29

B9(1 equivalent) and 9H-carbazole (9H-carbazole) (1.1 equivalent) produced in production example 4 were charged in dimethylacetamide (DMAc), and potassium phosphate (K) was added₃PO₄) (3 eq.) the mixture was heated under reflux and stirred. After 2 hours, the completion of the reaction was confirmed, and water was added, followed by filtration and recrystallization from chloroform and ethyl acetate, thereby producing the above-mentioned compound 29 (yield 69%, m)/z＝542.61)。

(2) Production of Compound 30

In the above (1), C4 produced in the above production example 5 was used in place of B9, and 2- (4- (9H-carbazol-2-yl) phenyl) -5-phenyl-1,3,4-

The above-mentioned compound 30 was produced in the same manner as the production method of the compound 29 of the above-mentioned (1) except that oxadiazole (2- (4- (9H-carbazol-2-yl) phenyl) -5-phenyl-1,3,4-oxadiazole) was used instead of 9H-carbazole (yield 58%, m/z: 618.71).

Compounds 31 to 34 were synthesized by the same method as the above-described compounds 1 to 30.

< example: production of organic light-emitting device >

Example 1.

ITO/Ag/ITO as anode is respectively added

The thickness of (2) is cut into a size of 50mm × 50mm × 0.5mm, and the substrate is placed in distilled water in which a dispersant is dissolved and washed by 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 anode thus prepared, the following HI-and

is formed by thermal vacuum evaporation, and on the hole injection layer, HT1 described below as a hole-transporting substance is formed in a thickness

The hole transport layer is formed by vacuum evaporation. Next, the following HT2 was used

A hole-controlling layer was formed by mixing the following BH1 as a host and the following BD1(2 wt%) as a dopant

The thickness of (2) is vacuum-evaporated to form a light-emitting layer. Then, the following ETM1 was added

The thickness of (3) was formed by vapor deposition, and the compound 1 produced in production example 9 and Liq below were mixed at a mass ratio of 7:3 to form a thickness

The electron transport layer of (1). In turn will

Magnesium and lithium fluoride (LiF) were formed in a thickness of 1:4 as an electron injection layer, and then as a cathode, magnesium and silver were formed in a thickness ratio of 1:4

After formation, CPL (Capping layer) of the cathode was formed using CP1 described below

Is evaporated to complete the device. In the above steps, the evaporation speed of the organic material is maintained

Examples 2 to 28 and 32 to 35

In example 1 described above, organic light-emitting devices of examples 2 to 28 and examples 32 to 35 were manufactured by the same method as in example 1 described above, except that compounds 2 to 28 and 31 to 34 manufactured in the above manufacturing example 9 were respectively used instead of compound 1 in forming an electron transport layer.

Example 29.

In example 1 above, except that the electron adjusting layer was not formed, in forming the electron transporting layer, the compound 16 produced in the above production example 9 was used instead of the compound 1 to

An organic light-emitting device was manufactured by the same method as in example 1 above, except that the thickness of (a) was not formed.

Example 30.

An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the compound 6 was used in place of ETM1 in forming the electron control layer, and the compound 14 was used in place of compound 1 in forming the electron transport layer.

Example 31.

An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the compound 24 was used in place of ETM1 in forming the electron control layer, and the compound 2 was used in place of compound 1 in forming the electron transport layer.

Comparative example 1 and comparative example 2.

Organic light-emitting devices of comparative examples 1 and 2 were produced in the same manner as in example 29 above, except that in example 29 above, the following ET1 and ET2 were used in place of compound 16, respectively, in forming the electron transport layer.

Comparative examples 3 to 8.

Organic light-emitting devices of comparative examples 3 to 8 were produced in the same manner as in example 1 above, except that in example 1 above, the following ET1 to ET6 were used in place of compound 1, respectively, in forming the electron transport layer.

For the organic light emitting devices of the above examples and comparative examples, the current will be at 20mA/cm²The results of measuring the properties such as voltage, luminous efficiency, color coordinates and lifetime at the current density of (A) are shown in Table 10 below. T95 is the time during which the measured luminance was 95% of the initial luminance.

[ Table 10]

From the results of table 10, it was confirmed that when the compound according to one embodiment of the present specification is contained in the electron adjusting layer and/or the electron transporting layer, the light emission efficiency and the lifetime are improved as compared with the case where the compound is not contained. In particular, a comparison between example 14 and example 30 and a comparison between example 2 and example 31 show that the performance is further improved when the above compound is contained in both the electron adjusting layer and the electron transporting layer. Specifically, in the case of comparative examples 1,3 and 5 using ET1 and ET3 containing triazine instead of pyrimidine of chemical formula 1 of the present application, no results were obtained

The structural combination of oxadiazole and pyrimidine is known to be inferior to the examples.

In addition, use

It is found that, in comparative examples 2 and 4 in which the substitution position of oxadiazole is different from ET2 in chemical formula 1, it is difficult to expect improvement of intramolecular polarity due to the asymmetric structure of azine group, and thus the performance is inferior to that in examples.

In addition, pyridine substituted instead of the chemical formula 1 of the present application is used

Comparative example 6, which is ET4 of oxadiazole (thiadiazole), failed to obtain

The structural combination of oxadiazole (thiadiazole) and pyrimidine revealed inferior performance compared to examples.

The ET5 used in comparative example 7 has pyrimidine (electron-withdrawing unit) introduced on both sides of thiadiazole, but it becomes a main factor for collapsing the balance of the entire device and cannot be coordinated with the energy levels of adjacent layers, thereby showing low efficiency, particularly low lifetime, while the ET6 used in comparative example 8 has no substituent introduced in pyrimidine, so that the electron-withdrawing unit has very low chemical stability, has a limitation in expressing aromatic characteristics, and thus shows low device performance.

Example 36.

ITO/Ag/ITO as anode is respectively added

The thickness of (2) is cut into a size of 50mm × 50mm × 0.5mm, and the substrate is placed in distilled water in which a dispersant is dissolved and washed by ultrasonic waves. The detergent was prepared from a product of Fisher Co, and the distilled water was filtered twice using a Filter (Filter) manufactured by Millipore CoThe distilled water of (1). After the anode was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. 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 anode thus prepared, the above HI-1 was added

Is formed by thermal vacuum evaporation, and on the hole injection layer, HT1 as a hole transport substance is deposited

The hole transport layer is formed by vacuum evaporation. Next, the HT2 was used

The hole-controlling layer was formed using the compound 25 synthesized in production example 9 and GH2 (1: 1 by weight) described below as the host, and GD1 (6% by weight) described below as the dopant, in an amount such that

The thickness of (2) is vacuum-evaporated to form a light-emitting layer. Then, the ETM1 was evaporated

An electron control layer was formed, and the following ET-A and the above Liq were mixed at a mass ratio of 7:3 to form a layer having a thickness

The electron transport layer of (1). In turn will

Magnesium and lithium fluoride (LiF) as an electron injection layer were formed in a thickness, and then magnesium and silver were formed in a thickness ratio of 1:4 as a cathode

After formation, CPL (cover layer) of the cathode was formed using the CP1 as described above

Example 37.

An organic light-emitting device was produced in the same manner as in example 36 except that in example 36, the above-mentioned compound 26 was used instead of the compound 25.

Comparative example 9.

An organic light-emitting device was produced in the same manner as in example 36 except that in example 36, the following GH1 was used instead of compound 25.

For the organic light emitting devices of examples 36 and 37 and comparative example 9 described above, the current would be at 20mA/cm²The results of measuring the properties such as voltage, luminous efficiency, color coordinates and lifetime at the current density of (A) are shown in Table 11 below. T95 is the time during which the measured luminance was 95% of the initial luminance.

[ Table 11]

From the results of table 11, it is understood that the case where the compound of chemical formula 1 of the present application is contained in the host differs from the case where it is not so implemented in the light emission efficiency and the lifetime. Specifically, it was confirmed that in the case of examples 36 and 37 in which the compound of chemical formula 1 was mainly contained, the luminous efficiency and the lifetime were greatly improved, but in the case of comparative example 9 not contained, the luminous efficiency and the lifetime were inferior to those of examples 36 and 37.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

x1 is O or S,

a to c are each independently an integer of 1 to 4,

2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

In the chemical formulas 1-1 to 1-4,

l1 to L3, Ar1 to Ar3, and a to c are the same as defined in the chemical formula 1.

3. The compound of claim 1, wherein said L3 is represented by any one of the following structural formulae:

in the structural formula, in the formula,

q1 to Q3 are each independently NR, CR 'R', O or S,

r, R 'and R' are each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, said R 'and R' being capable of bonding to each other to form a ring,

d2 is an integer from 0 to 2,

d3 is an integer from 0 to 3,

d4 is an integer from 0 to 4,

d5 is an integer from 0 to 5,

d6 is an integer from 0 to 6,

d7 is an integer from 0 to 7,

d1 is an integer from 1 to 4,

d is 1 or 2, and the compound has the structure of,

is a position connected to the chemical formula 1.

4. The compound of claim 1, wherein said Ar1 and Ar2 are each represented by any one of the following structural formulae:

in the structural formula, in the formula,

q4 is each independently NRa, CRbRc, O or S,

ra, Rb and Rc are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and Rb and Rc can be bonded to each other to form a ring,

d4 is an integer from 0 to 4,

d5 is an integer from 0 to 5,

d7 is an integer from 0 to 7,

d8 is an integer from 0 to 8,

d9 is an integer from 0 to 9,

e is an integer of 1 to 3,

is a position connected to the chemical formula 1.

5. The compound of claim 1, wherein Ar3 is hydrogen, a nitrile group, a linear or branched alkyl group, a monocyclic cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.

6. The compound of claim 1, wherein each of said L1 and L2 is independently a direct bond, a substituted or unsubstituted 2-valent phenyl group, a substituted or unsubstituted 2-valent biphenyl group, a substituted or unsubstituted 2-valent terphenyl group, a substituted or unsubstituted 2-valent anthracenyl group, or a substituted or unsubstituted 2-valent dibenzofuranyl group.

7. The compound of claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following structural formulas:

8. an organic light emitting device, comprising:

a first electrode;

a second electrode provided so as to face the first electrode; and

the organic light-emitting device includes 1 or more organic layers between the first electrode and the second electrode,

at least one of the organic layers comprises a compound of any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer containing the compound as a host.

10. The organic light-emitting device according to claim 8, wherein the organic layer comprises 1 or more electron transport layers, at least one of the electron transport layers containing the compound.

11. The organic light-emitting device according to claim 10, wherein the electron-transporting layer containing the compound further contains an organometallic complex.

12. The organic light emitting device of claim 8, wherein the organic layer comprises an emissive layer and an electron transport layer, the emissive layer and electron transport layer comprising the compound.

13. The organic light emitting device according to claim 8, wherein the organic layer comprises 1 or more electron-regulating layers, at least one of which contains the compound.

14. An organic light-emitting device according to claim 8 wherein the organic layer comprises an electron transport layer and an electron modulating layer, the electron transport layer and the electron modulating layer comprising the compound.