CN114364678A

CN114364678A - Compound and organic light emitting device including the same

Info

Publication number: CN114364678A
Application number: CN202080061153.0A
Authority: CN
Inventors: 金振珠; 全相映; 洪性佶; 崔愍偶; 全贤秀; 金宰垠
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-11-14
Filing date: 2020-11-13
Publication date: 2022-04-15
Also published as: KR102542198B1; WO2021096285A1; KR20210058727A

Abstract

The present specification provides a compound represented by 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 present application claims priority of korean patent application No. 10-2019-0145641, which was filed on 14.11.2019 to 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

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 the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.

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

Documents of the prior art

(patent document 1) laid-open patent publication No. 10-2015-0011347

Disclosure of Invention

Technical subject

Provided in the present specification are 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,

r is hydrogen, deuterium, 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, or combines with adjacent groups to form a substituted or unsubstituted ring,

r1 to R16, which are the same as or different from each other, are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring, at least one of R1 to R11 and R14 to R16 is represented by the following chemical formula 2,

[ chemical formula 2]

In the above-described chemical formula 2,

l1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

when any one of R1 to R8 is represented by chemical formula 2, R4 or R5 combines with R to form a substituted or unsubstituted ring,

indicates the position of binding to R1 to R11 and R14 to R16.

In addition, an embodiment of the present specification provides an organic light emitting device including: the organic light emitting device includes a first electrode, a second electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.

Effects of the invention

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment may achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting device. In particular, the compound described in the present specification can be used as a material for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, compared with the existing organic light emitting device, the organic light emitting device has the effects of low driving voltage, high efficiency or long service life.

Drawings

Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 9 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 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked.

Fig. 3 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked.

Fig. 4 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emission auxiliary layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked.

Description of the symbols

1: substrate

2: anode

3: hole injection layer

4: hole transport layer

5: electron blocking layer

6: luminescence auxiliary layer

7: luminescent layer

8: electron injection and transport layer

9: cathode electrode

Detailed Description

The present specification will be described in more detail below.

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.

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, examples of the substituent are described below, but the substituent is not limited thereto.

In the context of the present specification,

indicates a site to which another substituent or a binding moiety binds.

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, an amino group, a silyl group, a boron group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an aryl 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, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, a cycloalkyl group, an aryl 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.

Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the silyl group may be represented by-SiY_aY_bY_cThe above-mentioned chemical formula is Y_a、Y_bAnd Y_cMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. 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 this specification, the boron group may be represented BY-BY_dY_eThe above-mentioned chemical formula is Y_dAnd Y_eMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the oxygen of the ether group may be preferably substituted with a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms. In particular, the above-mentioned ether groups are, for example, -R_{Ether 0}-O-R_{Ether 1}Thus represented, R_{Ether 0}And R_{Ether 1}The alkyl group having 1 to 30 carbon atoms, the cycloalkyl group having 3 to 60 carbon atoms, or the aryl group having 6 to 60 carbon atoms may be used, but the present invention 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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

In the present specification, haloalkyl means an alkyl group substituted with a halogen group.

In the present specification, the above description of the alkyl group can be applied to the arylalkyl group except for the aryl group.

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, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.

The alkyl group, the alkoxy group and other substituents containing an alkyl moiety described in the present specification are all included in a linear or branched form.

In the present specification, haloalkoxy means alkoxy substituted with a halogen group.

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. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. 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 cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

In the present specification, the amino group is-NH₂The above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, or the like. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the amine group is 1 to 20. According to one embodiment, the number of carbon atoms of the amine group is 1 to 10. Specific examples of the substituted amino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a 9, 9-dimethylfluorenylphenylamino group, a pyridylphenylamino group, a diphenylamino group, a phenylpyridinylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a dibenzofuranylphenylamino group, a 9-methylanthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, and a diphenylamino group.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. As the above polycyclic aromatic group, may be mentionedNaphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl, perylene,

Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be

(9, 9-dimethylfluorenyl),

(9-methyl-9-phenylfluorenyl),

(9, 9-diphenylfluorenyl),

And the like, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group can be applied to the description about the aryl group described above.

In the present specification, the heterocyclic group includes N, O, P, S, Si and 1 or more of Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, benzofuryl, benzothienyl, dibenzofuryl, carbazolyl, dibenzothienyl, imidazolyl, pyrazolyl, and the like,

Azolyl radical, iso

Oxazolyl, thiazolyl, isothiazolyl, triazolyl,

Oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiapyranyl, pyrazinyl, pyranyl, thiadiazolyl, and thiadiazolyl,

oxazinyl, thiazinyl, di

Alkenyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolonoyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazindyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, benzothiazolyl, benzoxazolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, pyridopyrazinyl, naphthyridinyl, quinoxalinyl, xanthinyl, phenanthridinyl, quinoxalinyl, and a

Azolyl, benzimidazolyl, phenazinyl, imidazopyridinyl, pheno

Examples of the substituent include, but are not limited to, an oxazinyl group, a phenanthridinyl group, a phenanthrolinyl group, a phenothiazinyl group, an imidazopyridinyl group, an imidazophenanthridinyl group, a benzimidazoloquinazolinyl group, and a benzimidazolophenanthridinyl group.

In the present specification, sulfonyl is-SO₂R⁰Sulfinyl is-SOR⁰Sulfamoyl is-SO₂NR⁰The sulfonate group is-SO₃R⁰R is as defined above⁰Each independently is a linear or branched alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 40 carbon atoms, or a heteroaryl group having 2 to 40 carbon atoms. In one embodiment, R is⁰Each independently is a linear or branched alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

In the present specification, the heteroaryl group may be aromatic, and the above description about the heterocyclic group may be applied.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above in addition to the 2-valent group described above.

In the present specification, the meaning that adjacent groups are bonded to each other to form a ring is 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, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof. The above-mentioned hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocyclic ring includes at least 1 ring selected from N, O, P, S, Si and Se. In the present specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring means a ring which is not an aromatic ring and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.

In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, perylene, and the like,

Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc., but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocyclic ring means 1 out of 1 containing hetero atomsThe above aliphatic ring. Examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bis

Alkanes (1,4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxepane

Azacyclooctane

Thiocyclooctane

And the like, but is not limited thereto.

In the present specification, an aromatic heterocyclic ring means an aromatic ring containing 1 or more heteroatoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,

Oxazole, iso

Oxazole, thiazole, isothiazole, triazole, and the like,

Oxadiazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, pyridazines,

Oxazine, thiazine, II

Alkene, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaHeteroandene, indole, indolizine, benzothiazole, benzo

Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, thiophene

Oxazines, indolocarbazoles, indenocarbazoles, and the like, but are not limited thereto.

Preferred embodiments of the present invention will be described in detail below. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.

The present specification provides a compound represented by the following chemical formula 1. When the compound represented by the following chemical formula 1 is used for an organic layer of an organic light emitting device, the efficiency of the organic light emitting device is improved, and the compound has a low driving voltage and excellent life characteristics.

Chemical formula 1 according to the present invention is characterized in that amine groups including a fluorene group are combined in a spiroacridine fluorene structure through an o-phenylene group (chemical formula 2). In the case of the phenylene group having an amine group connected in an ortho position as in chemical formula 1, the HOMO level is relatively shallow and holes (holes) are easily transferred from a layer adjacent to an anode side, as compared with the compound having the phenylene group connected in a para (para) or meta (meta) position, and thus the voltage reduction effect is exhibited at the time of device driving. Furthermore, triplet energy is highest when having phenylene groups attached at ortho-positions, and thus electrons passing through the light emitting layer can be effectively blocked.

When the amine group contains a fluorene group, the mobility of holes is higher than when a general aryl group, for example, a biphenyl group, is connected, and the HOMO level adjustment is facilitated according to the bonding position of the fluorene group, and therefore, it is effective in matching the energy difference with the adjacent layer.

The following describes the chemical formula 1 in detail.

[ chemical formula 1]

In the above-described chemical formula 1,

[ chemical formula 2]

In the above-described chemical formula 2,

at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

indicates the position of binding to R1 to R11 and R14 to R16.

According to an embodiment of the present specification, R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, 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, or is combined with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or is directly bonded to each other with R4 or R5; or a ring containing O, S, N, P, C ═ O, C or Si is formed. In this case, the ring is substituted or unsubstituted with 1 or more substituents selected from the group consisting of hydrogen, alkyl groups, alkoxy groups, alkenyl groups, aryl groups, arylamine groups, heterocyclic groups, nitrile groups, amide groups, and ester groups, and the substituents may form a condensed ring and a spiro structure.

According to an embodiment of the present specification, R is a substituted or unsubstituted phenyl group, or forms a ring in combination with an adjacent group.

According to an embodiment of the present specification, R is a substituted or unsubstituted phenyl group, or combines with each other with adjacent groups to form a carbazole ring.

According to an embodiment of the present description, R is phenyl, or is combined with R4 or R5 to form a carbazole ring.

According to an embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is directly bonded to R4 or R5 to form a ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the above R is directly bonded to R4 or R5 to form a ring having 2 to 30 carbon atoms.

According to an embodiment of the present description, R is a substituted or unsubstituted phenyl and forms a direct bond with R4 or R5.

According to an embodiment of the present description, R is phenyl and forms a direct bond with R4 or R5.

According to an embodiment of the present description, R is phenyl.

According to an embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently represents hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to one embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the others are the same as or different from each other, each independently hydrogen or deuterium, or combine with adjacent groups to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the others are the same as or different from each other, and each independently hydrogen or deuterium, or combine with adjacent groups to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the others are the same or different from each other and each independently hydrogen or deuterium, and R4 and R5 may be directly bonded to R to form a substituted or unsubstituted carbazole ring.

According to an embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the others are the same or different from each other and are each independently hydrogen or deuterium, and R4 and R5 may be directly bonded to R to form a carbazole ring.

According to an embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the remainder is hydrogen, and R4 and R5 may be directly bonded to R to form a carbazole ring.

According to an embodiment of the present specification, at least one of R1 to R3, R5 to R11, and R14 to R16 is represented by the above chemical formula 2, and the remainder is hydrogen, and R4 may combine with R to form a carbazole ring.

According to one embodiment of the present disclosure, R4 and R combine with each other to form a carbazole ring.

According to one embodiment of the present disclosure, R5 and R combine with each other to form a carbazole ring.

According to an embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the above chemical formula 2, and the rest not represented by the above chemical formula 2 is hydrogen.

According to an embodiment of the present description, R12 and R13 are hydrogen or deuterium.

According to an embodiment of the present description, R12 and R13 are hydrogen.

According to an embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by the following chemical formula 2.

[ chemical formula 2]

In the above-described chemical formula 2,

at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

indicates the position of binding to R1 to R11 and R14 to R16.

According to an embodiment of the present specification, L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 30 carbon atoms.

According to an embodiment of the present specification, L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 20 carbon atoms.

According to an embodiment of the present specification, L1 and L2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, L1 and L2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an embodiment of the present description, L1 and L2, equal to or different from each other, are each independently a direct bond or an arylene group.

According to an embodiment of the present specification, L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

According to an embodiment of the present description, L1 and L2, equal to or different from each other, are each independently a direct bond, phenylene or biphenylene.

According to an embodiment of the present description, L1 and L2, equal to or different from each other, are each independently a direct bond or a phenylene group.

According to an embodiment of the present description, L1 and L2, equal to or different from each other, are each independently a direct bond, an ortho-phenylene, a meta-phenylene, or a para-phenylene.

According to an embodiment of the present disclosure, L1 and L2 are the same or different from each other, and are each independently a direct bond.

According to an embodiment of the present description, L1 and L2, equal to or different from each other, are each independently phenylene.

According to an embodiment of the present specification, L1 and L2 are the same as or different from each other, and each is independently a direct bond, or represented by any one of the following structural formulae.

In the above structural formulae, the dotted line represents a binding site.

According to one embodiment of the present description, L1 is a direct bond or phenylene.

According to one embodiment of the present description, L1 is a direct bond or p-phenylene.

According to one embodiment of the present description, L2 is a direct bond or phenylene.

According to one embodiment of the present description, L2 is a direct bond or p-phenylene.

According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently 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 specification, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently an aryl group substituted or unsubstituted with an alkyl group or an aryl group.

According to an embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 30 carbon atoms.

According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each 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, or a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group, a biphenyl group substituted or unsubstituted with an alkyl group or an aryl group, a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group substituted or unsubstituted with a methyl group.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, or a dimethylfluorenyl group.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each is independently represented by any one of the following structural formulae.

In the above structural formulae, the dotted line represents a binding site.

According to an embodiment of the present description, Ar1 is a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present description, Ar1 is a fluorenyl group substituted or unsubstituted with an alkyl or aryl group.

According to an embodiment of the present specification, Ar1 is a fluorenyl group substituted or unsubstituted with an alkyl group.

According to an embodiment of the present description, Ar1 is dimethylfluorenyl.

According to one embodiment of the present description, Ar2 is a substituted or unsubstituted aryl group.

According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present specification, Ar2 is a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

According to an embodiment of the present specification, Ar2 is a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group.

According to an embodiment of the present description, Ar2 is phenyl, biphenyl, or dimethylfluorenyl.

According to an embodiment of the present description, at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present description, at least one of Ar1 and Ar2 is a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

According to an embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present description, at least one of Ar1 and Ar2 is a dimethylfluorenyl group.

According to an embodiment of the present disclosure, Ar1 is a substituted or unsubstituted fluorenyl group and Ar2 is a substituted or unsubstituted aryl group.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group, and Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

According to an embodiment of the present specification, Ar1 is a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group, and Ar2 is a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

According to an embodiment of the present specification, Ar1 is a fluorenyl group substituted or unsubstituted with an alkyl group, and Ar2 is a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present disclosure, Ar1 is a dimethylfluorenyl group, and Ar2 is a phenyl group, a biphenyl group, or a dimethylfluorenyl group.

According to one embodiment of the present disclosure, Ar1 is a dimethylfluorenyl group and Ar2 is a phenyl group.

According to one embodiment of the present disclosure, Ar1 is a dimethylfluorenyl group and Ar2 is a biphenyl group.

According to an embodiment of the present description, Ar1 and Ar2 are dimethylfluorenyl.

According to an embodiment of the present specification, when any one of R1 to R8 is represented by chemical formula 2, R4 or R5 is directly bonded to R to form a substituted or unsubstituted ring.

According to an embodiment of the present specification, when any one of R1 to R8 is represented by chemical formula 2, R4 or R5 is directly bonded to R to form a carbazole ring.

According to an embodiment of the present specification, when any one of R1 to R3 and R5 to R8 is represented by chemical formula 2, R4 and R are directly bonded to form a carbazole ring.

According to an embodiment of the present specification, when any one of R1 to R4 and R6 to R8 is represented by chemical formula 2, R5 and R are directly bonded to form a carbazole ring.

According to an embodiment of the present disclosure, the chemical formula 2 is represented by the following chemical formula 2-1.

[ chemical formula 2-1]

In the above chemical formula 2-1, L1, L2 and Ar2 are defined as in chemical formula 2,

ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted alkyl group. According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted methyl group.

According to an embodiment of the present description, Ar3 and Ar4 are methyl.

According to an embodiment of the present specification, the chemical formula 2 is represented by any one of the following chemical formulas 2-1-1 to 2-1-4.

[ chemical formula 2-1-1]

[ chemical formula 2-1-2]

[ chemical formulas 2-1-3]

[ chemical formulas 2-1-4]

In the above chemical formulas 2-1-1 to 2-1-4, L1, L2, and Ar2 to Ar4 are defined as in chemical formula 2.

According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the above chemical formula 1-1,

g1 to G3 and G5 to G16, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring.

At least one of G1 to G3, G5 to G11, and G14 to G16 is represented by the above chemical formula 2.

In one embodiment of the present specification, at least one of G1 to G3, G5 to G11, and G14 to G16 is represented by the above chemical formula 2, and the others are the same as or different from each other, and each is independently hydrogen or deuterium.

In one embodiment of the present specification, at least one of G1 to G3, G5 to G11, and G14 to G16 is represented by the above chemical formula 2, and the rest is hydrogen.

In one embodiment of the present specification, any one of G1 to G3, G5 to G11, and G14 to G16 is represented by the above chemical formula 2, and the remainder is hydrogen.

In one embodiment of the present specification, at least one of G1 to G3 and G5 to G8 is represented by the above chemical formula 2.

In one embodiment of the present specification, at least one of G1 to G3 is represented by the above chemical formula 2.

In one embodiment of the present specification, at least one of G5 to G8 is represented by the above chemical formula 2.

In one embodiment of the present specification, G5 is represented by chemical formula 2.

In one embodiment of the present specification, G6 is represented by chemical formula 2.

In one embodiment of the present specification, G7 is represented by chemical formula 2.

In one embodiment of the present specification, G8 is represented by chemical formula 2.

In one embodiment of the present specification, at least one of G9 to G11 and G14 to G16 is represented by the above chemical formula 2.

In one embodiment of the present specification, G14 is represented by chemical formula 2.

In one embodiment of the present specification, G15 is represented by chemical formula 2.

In one embodiment of the present specification, G16 is represented by chemical formula 2.

In one embodiment of the present disclosure, the definitions of G1-G16 may be applied to the definitions of R1-R16.

According to an embodiment of the present disclosure, the chemical formula 1 is represented by the following chemical formula 1-2.

[ chemical formulas 1-2]

In the above chemical formula 1-2,

y1 to Y16 are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring, and at least one of Y9 to Y11 and Y14 to Y16 is represented by the above chemical formula 2.

In one embodiment of the present specification, Y1 to Y8, Y12 and Y13 are the same or different from each other, and each is independently hydrogen or deuterium.

In one embodiment of the present specification, Y1 to Y8, Y12 and Y13 are hydrogen.

In one embodiment of the present specification, at least one of Y9 to Y11 and Y14 to Y16 is represented by the above chemical formula 2, and the others are the same as or different from each other, and each is independently hydrogen or deuterium.

In one embodiment of the present specification, at least one of Y9 to Y11 and Y14 to Y16 is represented by the above chemical formula 2, and the rest is hydrogen.

In one embodiment of the present specification, any one of Y9 to Y11 and Y14 to Y16 is represented by the above chemical formula 2, and the remainder is hydrogen.

In one embodiment of the present specification, Y9 is represented by chemical formula 2.

In one embodiment of the present specification, Y10 is represented by chemical formula 2.

In one embodiment of the present specification, Y11 is represented by chemical formula 2.

In one embodiment of the present specification, Y14 is represented by chemical formula 2.

In one embodiment of the present specification, Y15 is represented by chemical formula 2.

In one embodiment of the present specification, Y16 is represented by chemical formula 2.

In one embodiment of the present disclosure, the definitions of Y1 to Y16 may be applied to the definitions of R1 to R16.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-7.

[ chemical formula 3-1]

[ chemical formula 3-2]

[ chemical formulas 3-3]

[ chemical formulas 3-4]

[ chemical formulas 3-5]

[ chemical formulas 3-6]

[ chemical formulas 3 to 7]

In the above chemical formulas 3-1 to 3-7, R1 to R3 and R5 to R16 are defined as in chemical formula 1, and L1, L2, Ar1 and Ar2 are defined as in chemical formula 2.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 4-1 to 4-3.

[ chemical formula 4-1]

[ chemical formula 4-2]

[ chemical formulas 4-3]

In the above chemical formulas 4-1 to 4-3, R1 to R16 are defined as in chemical formula 1, and L1, L2, Ar1 and Ar2 are defined as in chemical formula 2.

According to an embodiment of the present disclosure, the chemical formula 1 may be represented by any one of the following structural formulae.

The compound represented by chemical formula 1 according to one embodiment of the present specification can be produced into a core structure as in the production example described later. The substituents may be combined 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.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In the present invention, the HOMO and LUMO levels of the compound can also be adjusted by introducing various substituents into the core structure of the above-described structure.

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

In one embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

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 specification, the organic light emitting device 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, an electron blocking layer, a hole blocking layer, and the like as an organic layer. 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 disclosure, the organic layer includes a light emitting layer, and the light emitting layer may include a compound represented by the chemical formula 1.

In one embodiment of the present specification, the light-emitting layer may further contain a phosphorescent substance or a delayed fluorescence compound. The delayed fluorescence compound is a light-emitting organic compound having an energy gap (Δ Est) between the lowest triplet state T1 and the first excited singlet state S1 of 0.2eV or less.

When the energy gap (Δ Est) between the first excited singlet state S1 and the lowest triplet state T1 of the delayed fluorescent compound satisfies the above range, the rate and speed at which excitons generated in the triplet state migrate to the singlet state through reverse intersystem crossing (RISC) are increased, thereby reducing the time during which the excitons stay in the triplet state, and thus there is an advantage in that the efficiency and lifetime of the organic light emitting device are increased.

In one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, or a light emission auxiliary layer, and the hole injection layer, the hole transport layer, the hole injection and transport layer, the electron blocking layer, or the light emission auxiliary layer of the organic layer includes the compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound represented by chemical formula 1.

In one embodiment of the present disclosure, the organic layer includes a hole injection layer, and the hole injection layer includes a compound represented by the chemical formula 1.

In one embodiment of the present disclosure, the organic layer includes a hole transport layer, and the hole transport layer includes a compound represented by the chemical formula 1.

In one embodiment of the present disclosure, the organic layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by the chemical formula 1.

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

In the organic light emitting device of the present specification, the organic layer includes a hole transport layer and a hole injection layer, and the hole transport layer and the hole injection layer may each include a compound represented by the above chemical formula 1.

In one embodiment of the present specification, the organic layer is a hole injection layer, and the hole injection layer includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic layer is a hole transport layer, and the hole transport layer includes a compound represented by the chemical formula 1.

In one embodiment of the present disclosure, the organic layer is an electron blocking layer, and the electron blocking layer includes a compound represented by the chemical formula 1.

In one embodiment of the present disclosure, the organic layer is a light-emitting auxiliary layer, and the light-emitting auxiliary layer includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic layer including the compound represented by the above chemical formula 1 may have a thickness of

To

Or

To

Or

To

In another embodiment, the organic layer including the compound represented by the above chemical formula 1 may have a thickness of

To

Or

To

Or

To

In another embodiment, the organic layer may further include a metal or a metal compound in addition to the compound represented by the chemical formula 1.

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

In one embodiment of the present specification, the organic light emitting device includes a first electrode, a second electrode, a light emitting layer disposed between the first electrode and the second electrode, and 2 or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the 2 or more organic layers includes the compound represented by chemical formula 1.

In one embodiment of the present specification, the organic light emitting device includes a first electrode, a second electrode, a light emitting layer disposed between the first electrode and the second electrode, and 2 or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least 2 of the 2 or more organic layers include the compound represented by chemical formula 1.

In one embodiment of the present specification, the 2 or more organic layers may be 2 or more selected from a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that simultaneously performs hole transport and hole injection, and an electron-blocking layer.

In one embodiment of the present specification, the 2 or more organic layers may be 2 or more selected from a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, an electron adjustment layer, and a hole blocking layer.

In one embodiment of the present disclosure, the organic layer includes 1 or more hole injection layers and 1 or more hole transport layers, and at least one of the 1 or more hole injection layers and the 1 or more hole transport layers includes the compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the above chemical formula 1 may be included in 1 layer of 1 or more hole injection layers and 1 or more hole transport layers, and may be included in each of 1 or more hole injection layers and 1 or more hole transport layers.

In another embodiment, the organic layer including the compound represented by the above chemical formula 1 may include an additional organic compound. For example, the organic layer including the compound represented by the above chemical formula 1 may further include 4- [ [2,3-bis [ cyano- (4-cyano-2,3,5,6-tetrafluorophenyl) methylene ] cyclopropyl ] -cyanomethyl ] -2,3,5,6-tetrafluorobenzonitrile (4- [ [2,3-bis [ cyano- (4-cyano-2,3,5,6-tetrafluorophenyl) methylidene ] cyclopropyrene ] -cyclomethenyl ] -2,3,5, 6-tetrafluorobenzonitrile). According to an example, the compound represented by the above chemical formula 1 and the above organic compound may be included in a weight ratio of 100:0.1 to 100:30, for example, 100:1 to 100: 10.

In one embodiment of the present disclosure, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes the compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the above chemical formula 1 may be contained in 1 layer of the 2 or more hole transport layers, and may be contained in each of the 2 or more hole transport layers.

In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.

In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by chemical formula 1.

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.

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present disclosure, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 to 4 illustrate the structure of an organic light emitting device according to an embodiment of the present specification. The organic light emitting device is illustrated in fig. 1 to 4, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 9 are sequentially stacked. In the structure as described above, the above-described compound may be contained in the above-described light-emitting layer 7.

Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure as described above, the above compound may be contained in 1 or more of the above hole injection layer 3, hole transport layer 4, electron blocking layer 5, light emitting layer 7, and electron injection and transport layer 8.

Fig. 3 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure as described above, the above compound may be contained in 1 or more of the above hole injection layer 3, hole transport layer 4, light emitting layer 7, and electron injection and transport layer 8.

Fig. 4 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emission auxiliary layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure as described above, the above compound may be contained in 1 or more of the above hole injection layer 3, hole transport layer 4, light emission auxiliary layer 6, light emitting layer 7, and electron injection and transport layer 8.

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 of the organic layers include the above compound, i.e., the compound represented by the above chemical formula 1.

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. In this case, the following production can be performed: 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, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.

In addition, the compound represented by the above chemical formula 1 may be formed into 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, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device. However, the production method is not limited thereto.

The first electrode material is usually used for making a voidThe hole can be smoothly injected into the organic layer, and is preferably a substance having a large work function. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., 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 second electrode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The light emitting layer may comprise additional host and dopant materials. The host material may be an aromatic fused ring derivative or a heterocyclic ring-containing compound. Specifically, the aromatic condensed 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 dibenzofuran derivative and a ladder-type furan compound

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

As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, 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. Further, the styrylamine compound is a compound substituted with at least a substituted or unsubstituted arylamine1 arylethenyl compound, 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 the present specification, when an additional light-emitting layer is provided, the light-emitting substance of the light-emitting layer is a substance which 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. For example, there are 8-hydroxy-quinoline aluminum complexes (Alq 3); 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; a polyfluorene; and rubrene, but the present invention is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. The hole injection substance is preferably as follows: has the ability to transport holes, has the effect of injecting holes from the first electrode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, a substance excellent in the ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film-forming ability is preferable. Further, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the first electrode 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; a carbazole-based organic substance; a nitrile-based organic compound; hexanenitrile hexaazatriphenylene series organic matter; quinacridone (quinacridone) -based organic compounds; perylene (perylene) -based organic compounds; anthraquinone, polyaniline, and polythiophene-based conductive polymers, or a mixture of 2 or more of the above-mentioned examples, but the present invention is not limited thereto. In addition, the compound represented by the above chemical formula 1 may be used.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is a substance capable of receiving holes from the first electrode 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 substances, carbazole-based organic substances, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously. In addition, the compound represented by the above chemical formula 1 may be used.

The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the second electrode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, LiQ, and the like. The electron transport layer may be used with any desired first electrode material as used in the art. Suitable first electrode substances are, in particular, the usual 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 electrode. The electron-injecting substance is preferably as follows: a substance having an excellent ability to transport electrons, having an effect of injecting electrons from the second electrode, and having an excellent electron injection effect for the light-emitting layer or the light-emitting material. Further, it is preferable that the material prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and has excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, triazine, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, and mixtures of 2 or more of the above examples, but 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 electron blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, so that the lifetime and efficiency of the device can be improved. Any known material can be used without limitation, and the light-emitting layer and the hole-injecting layer or the light-emitting layer and the layer which performs hole injection and hole transport simultaneously can be formed therebetween.

The hole blocking layer is a layer that prevents holes from reaching the second electrode, 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, an aluminum complex (aluminum complex), pyridine, pyrimidine, or triazine derivative, and the like, but is not limited thereto.

The electron control layer is a layer for controlling the migration of electrons to the light-emitting layer, and materials known in the art can be used.

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.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

The compound according to the present specification can also function in an organic light-emitting device typified by an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, or the like, according to a principle similar to that applied to the organic light-emitting device. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer disposed between the cathode and the anode, and the photoactive layer may include the compound.

Modes for carrying out the invention

Hereinafter, in order to specifically explain the present specification, the details will be explained by referring to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.

< Synthesis example >

[ Synthesis example 1] Synthesis of Compound 1

10.0g (20.64mmol) of the above 12'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] (12'-bromospiro [ fluoro-9, 8' -indolo [3,2,1-de ] acridine ]), 8.37g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (phenyl) amino) phenyl) boronic acid (2- ((9, 9-dimethyl-9H-fluoro-2-yl) (phenyl) amino) phenyl) boronic acid) and 2 mol% of tetrakis (triphenylphosphine) palladium were added to 80ml of tetrahydrofuran, and 8.56g (61.92mmol) of potassium carbonate (potassium carbonate) was dissolved in 40ml of water and stirred. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirring was performed, and after filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure. Then, column purification was performed, whereby 11.37g of compound 1 was obtained (yield 72%).

MS:[M+H]⁺＝765

[ Synthesis example 2] Synthesis of Compound 2

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 12'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid (2- ([1,1' -biphenyl ] -4-yl (9, 9-dimethyl-9H-fluoro-3-yl) amino) phenyl) boronic acid), and purifying was carried out to obtain 12.15g of the compound 2 (yield 70%).

MS:[M+H]⁺＝842

[ Synthesis example 3] Synthesis of Compound 3

Using 10.0g (20.64mmol) of the above-mentioned 11'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] (11'-bromospiro [ fluorone-9, 8' -indolo [3,2,1-de ] acridine ]) and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid ((2- ([1,1' -biphenyl ] -4-yl (9, 9-dimethyl-9H-fluoron-2-yl) amino) phenyl) boronic acid), the reaction was carried out in the same manner as in the synthesis of the above compound 1, and purification was carried out, whereby 13.02g of compound 3 was obtained (yield 75%).

MS:[M+H]⁺＝842

[ Synthesis example 4] Synthesis of Compound 4

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 11'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -3-yl (9,9-dimethyl-9H-fluoren-4-yl) amino) phenyl) boronic acid ((2- ([1,1' -biphenyl ] -3-yl (9, 9-dimethyl-9H-fluoro-4-yl) amin o) phenyl) boronic acid), and purification was carried out to obtain 13.02g of the compound 4 (yield 75%).

MS:[M+H]⁺＝842

[ Synthesis example 5] Synthesis of Compound 5

Using 10.0g (20.64mmol) of the above-mentioned 10'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] (10'-bromospiro [ fluorone-9, 8' -indolo [3,2,1-de ] acridine ]) and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -2-yl (9,9-dimethyl-9H-fluoren-1-yl) amino) phenyl) boronic acid ((2- ([1,1' -biphenyl ] -2-yl (9, 9-dimethyl-9H-fluoron-1-yl) amino) phenyl) boronic acid), the reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, and purification was carried out, whereby 11.80g of compound 5 was obtained (yield 68%).

MS:[M+H]⁺＝842

[ Synthesis example 6] Synthesis of Compound 6

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 10' -bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out, thereby obtaining 12.85g of a compound 6 (yield 74%).

MS:[M+H]⁺＝842

[ Synthesis example 7] Synthesis of Compound 7

The reaction was carried out and the purification was carried out in the same manner as the synthesis of the above-mentioned compound 1, except for using 10.0g (20.64mmol) of the above-mentioned 9' -bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] (9' -bromospiro [ fluoro [3,2,1-de ] acridine ] (9' -fluorospiro [ fluorone-9, 8' -indolo [3,2,1-de ] acridine ] (9' -bromospiro [3,2,1-de ] acridine ] (9' -dimethyl-9H-fluoren-2-yl) phenyl) (phenyl) amino) phenyl) boronic acid ((2- ((4- (9, 9-dimethyl-9H-fluoro-2-yl) phenyl) (phenyl) amino) phenyl) boronic acid) (20.64mmol), thereby obtaining 11.46g of the compound 7 (yield 66%).

MS:[M+H]⁺＝842

[ Synthesis example 8] Synthesis of Compound 8

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, and purification was carried out, except for using 10.0g (20.64mmol) of the above-mentioned 9'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 8.37g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-4-yl) (phenyl) amino) phenyl) boronic acid ((2- ((9, 9-dimethyl-9H-fluoro-4-yl) (phenyl) amino) phenyl) boronic acid), whereby 11.20g of the compound 8 was obtained (yield 71%).

MS:[M+H]⁺＝765

[ Synthesis example 9] Synthesis of Compound 9

Using 10.0g (20.64mmol) of the above-mentioned 1-bromospiro [ fluorene-9,8'-indolo [3,2,1-de ] acridine ] (1-bromospiro [ fluoroene-9, 8' -indolo [3,2,1-de ] acridine ]) and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -2-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid ((2- ([1,1' -biphenyl ] -2-yl (9, 9-dimethyl-9H-fluoroen-2-yl) amino) phenyl) boronic acid), the reaction was carried out in the same manner as in the synthesis of the above compound 1, and purification was carried out, whereby 9.37g of compound 9 was obtained (yield 59%).

MS:[M+H]⁺＝842

Synthesis example 10 Synthesis of Compound 10

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, except for using 10.0g (20.64mmol) of the above-mentioned 1-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ((4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) (phenyl) amino) phenyl) boronic acid, and purification was carried out, thereby obtaining 9.15g of compound 10 (yield 58%).

MS:[M+H]⁺＝765

[ Synthesis example 11] Synthesis of Compound 11

The reaction was carried out in the same manner as the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 2-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] (2-bromospiro [ fluoroene-9, 8' -indolo [3,2,1-de ] acridine ]) and 9.94g (20.64mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out to obtain 12.50g of the compound 11 (yield 72%).

MS:[M+H]⁺＝842

Synthesis example 12 Synthesis of Compound 12

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, except for using 10.0g (20.64mmol) of the above-mentioned 2-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ((4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) (phenyl) amino) phenyl) boronic acid, and purifying, thereby obtaining 12.67g of the compound 12 (yield 73%).

MS:[M+H]⁺＝842

[ Synthesis example 13] Synthesis of Compound 13

Using 10.0g (20.64mmol) of the above-mentioned 3-bromospiro [ fluorene-9,8'-indolo [3,2,1-de ] acridine ] (3-bromospiro [ fluoroene-9, 8' -indolo [3,2,1-de ] acridine ]) and 9.94g (20.64mmol) of (2- ([1,1'-biphenyl ] -3-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid ((2- ([1,1' -biphenyl ] -3-yl (9, 9-dimethyl-9H-fluoroen-2-yl) amino) phenyl) boronic acid), the reaction was carried out in the same manner as in the synthesis of the above compound 1, and purification was carried out, whereby 12.15g of compound 13 was obtained (yield 70%).

MS:[M+H]⁺＝842

Synthesis example 14 Synthesis of Compound 14

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 3-bromospiro [ fluorene-9,8'-indolo [3,2,1-de ] acridine ] and 9.94g (20.64mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out, thereby obtaining 12.32g of the compound 14 (yield 70%).

MS:[M+H]⁺＝842

[ Synthesis example 15] Synthesis of Compound 15

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 and purification was carried out by using 10.0g (20.56mmol) of the above-mentioned 1'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] (1'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ]) and 8.33g (20.56mmol) of (2- ((9,9-dimethyl-9H-fluoren-3-yl) (phenyl) amino) phenyl) boronic acid ((2- ((9, 9-dimethyl-9H-fluoro-3-yl) (phenyl) amino) phenyl) boronic acid), thereby obtaining 8.67g of a compound 15 (yield 55%).

MS:[M+H]⁺＝767

Synthesis example 16 Synthesis of Compound 16

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, except for using 10.0g (20.56mmol) of the above-mentioned 1' -bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 9.90g (20.56mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out, thereby obtaining 9.01g of the compound 16 (yield 51%).

MS:[M+H]⁺＝844

[ Synthesis example 17] Synthesis of Compound 17

The reaction was carried out in the same manner as the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 2' -bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] (2' -bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ]) and 9.90g (20.56mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purifying, thereby obtaining 12.30g of the compound 17 (yield 71%).

MS:[M+H]⁺＝844

[ Synthesis example 18] Synthesis of Compound 18

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 2'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 9.90g (20.56mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (phenyl) amino) phenyl) boronic acid, and purifying, thereby obtaining 11.67g of a compound 18 (yield 74%).

MS:[M+H]⁺＝767

[ Synthesis example 19] Synthesis of Compound 19

The reaction was carried out in the same manner as the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 3' -bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] (3' -bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ]) and 9.90g (20.56mmol) of (2- ([1,1' -biphenyl ] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purifying, thereby obtaining 12.13g of the compound 19 (yield 70%).

MS:[M+H]⁺＝844

[ Synthesis example 20] Synthesis of Compound 20

The reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 3'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 9.90g (20.56mmol) of (2- ((4- (9,9-dimethyl-9H-fluoren-1-yl) phenyl) (phenyl) amino) phenyl) boronic acid ((2- ((4- (9, 9-dimethyl-9H-fluoro-1-yl) phenyl) (phenyl) amino) phenyl) boronic acid), thereby obtaining 11.78g of the compound 20 (yield 68%).

MS:[M+H]⁺＝844

Synthesis example 21 Synthesis of Compound 21

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 12'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid ((2- (bis (9, 9-dimethyl-9H-fluoro-2-yl) amino) phenyl) boronic acid), and purifying it, thereby obtaining 10.73g of the compound 21 (yield 59%).

MS:[M+H]⁺＝882

[ Synthesis example 22] Synthesis of Compound 22

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 11'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out to obtain 11.05g of the compound 22 (yield 61%).

MS:[M+H]⁺＝882

[ Synthesis example 23] Synthesis of Compound 23

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 10'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out to obtain 11.42g of a compound 23 (yield 63%).

MS:[M+H]⁺＝882

Synthesis example 24 Synthesis of Compound 24

9.42g of Compound 24 (yield 52%) was obtained by conducting a reaction and purification in the same manner as in the synthesis of Compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 9'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid ((2- (bis (9, 9-dimethyl-9H-fluoro-3-yl) amino) phenyl) boronic acid).

MS:[M+H]⁺＝882

Synthesis example 25 Synthesis of Compound 25

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 10'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid ((2- ((9, 9-dimethyl-9H-fluoro-2-yl) (9, 9-dimethyl-9H-fluoro-3-yl) amino) phenyl) boronic acid), and purifying, thereby obtaining 11.23g of the compound 25 (yield 62%).

MS:[M+H]⁺＝882

[ Synthesis example 26] Synthesis of Compound 26

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 9'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-3-yl) (9,9-dimethyl-9H-fluoren-4-yl) amino) phenyl) boronic acid ((2- ((9, 9-dimethyl-9H-fluoro-3-yl) (9, 9-dimethyl-9H-fluoro-4-yl) amino) phenyl) boronic acid), and purifying, thereby obtaining 9.06g of the compound 26 (yield 50%).

MS:[M+H]⁺＝882

[ Synthesis example 27] Synthesis of Compound 27

A reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1, except for using 10.0g (20.64mmol) of the above-mentioned 1-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (9,9-dimethyl-9H-fluoren-4-yl) amino) phenyl) boronic acid ((2- ((9, 9-dimethyl-9H-fluoro-2-yl) (9, 9-dimethyl-9H-fluoro-4-yl) amino) phenyl) boronic acid), and purifying it, thereby obtaining 10.33g of the compound 27 (yield 57%).

MS:[M+H]⁺＝882

Synthesis example 28 Synthesis of Compound 28

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 2-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purification was carried out to obtain 11.23g of the compound 28 (yield 62%).

MS:[M+H]⁺＝882

Synthesis example 29 Synthesis of Compound 29

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 3-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 10.76g (20.64mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid, and purification was carried out to obtain 11.60g of a compound 29 (yield 64%).

MS:[M+H]⁺＝882

[ Synthesis example 30] Synthesis of Compound 30

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 1'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 10.72g (20.56mmol) of (2- ((9,9-dimethyl-9H-fluoren-1-yl) (9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid ((2- ((9,9-dimethyl-9H-fluoren-1-yl) (9, 9-dimethyl-9H-fluoro-3-yl) amino) phenyl) boronic acid), and purification was carried out to obtain 9.24g of the compound 30 (yield 51%).

MS:[M+H]⁺＝884

[ Synthesis example 31] Synthesis of Compound 31

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 2'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 10.72g (20.56mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purifying was carried out to obtain 11.99g of the compound 31 (yield 66%).

MS:[M+H]⁺＝884

[ Synthesis example 32] Synthesis of Compound 32

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.56mmol) of the above-mentioned 3'-bromo-10-phenyl-10H-spiro [ acridine-9,9' -fluorene ] and 10.72g (20.56mmol) of (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, and purifying them, thereby obtaining 11.44g of a compound 32 (yield 63%).

MS:[M+H]⁺＝884

Synthesis example 33 Synthesis of Compound 33

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 10'-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 8.37g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (phenyl) amino) phenyl) boronic acid, and purification was carried out to obtain 10.41g of a compound 33 (yield 64%).

MS:[M+H]⁺＝765

[ Synthesis example 34] Synthesis of Compound 34

The reaction was carried out in the same manner as in the synthesis of the above-mentioned compound 1 except for using 10.0g (20.64mmol) of the above-mentioned 2-bromospiro [ fluorene-9,8' -indolo [3,2,1-de ] acridine ] and 8.37g (20.64mmol) of (2- ((9,9-dimethyl-9H-fluoren-2-yl) (phenyl) amino) phenyl) boronic acid, and purification was carried out to obtain 11.04g of the compound 34 (yield 70%).

MS:[M+H]⁺＝765

< Experimental example >

< Experimental examples 1-1>

Indium Tin Oxide (ITO) and a process for producing the same

Is coated to a thickness ofThe glass substrate of the thin film was washed with ultrasonic waves by putting it in distilled water in which a detergent was dissolved. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using 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, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, compound 1 produced according to synthesis example 1 above and a compound of the following formula HI-a were vacuum-evaporated at a weight ratio of 100:3 to prepare an ITO transparent electrode

The thickness of (3) forms a hole injection layer.

On the hole injection layer, compound 1 produced according to synthesis example 1 was used as a hole-transporting substance, and

the hole transport layer is formed by vacuum evaporation.

Then, on the hole transport layer, the film thickness

The electron blocking layer was formed by vacuum evaporation of EB1(TCTA) described below.

Then, on the electron blocking layer, the film thickness

The light-emitting layer was formed by vacuum evaporation of BH and BD shown below at a weight ratio of 25: 1.

On the light-emitting layer, ET1 and LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to form a layer

The thickness of (a) forms an electron injection and transport layer.

On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to

Thickness of aluminum and

the thickness of (3) is evaporated to form a cathode.

In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4

Sec, maintenance of lithium fluoride at the cathode

Evaporation Rate,/sec, aluminum maintenance

A vapor deposition rate of/sec, and a degree of vacuum of 2X 10 was maintained during vapor deposition^-7～5×10^-6And supporting to thereby fabricate an organic light emitting device.

< Experimental examples 1-2 to 1-34>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in the above experimental example 1-1, the compounds shown in table 1 below were used instead of compound 1.

< comparative examples 1-1 and 1-2>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in the above experimental example 1-1, the following comparative example compounds HT1 and HT2 were used, respectively, instead of compound 1.

[ Table 1]

From the results of table 1 described above, experimental examples 1-1 to 1-34 using the compound represented by chemical formula 1 according to the present invention for the hole injection layer and/or the hole transport layer showed results that the driving voltage and the efficiency characteristics were excellent as a whole, as compared to comparative examples 1-1 to and 1-2.

Specifically, experimental examples 1-1 to 1-34 showed the results of a maximum decrease in voltage of about 24% and a maximum increase in efficiency of about 15% as compared to comparative examples 1-1 and 1-2 using a compound not including a fluorenyl group or having a different binding site of chemical formula 2 from that of the present invention.

Accordingly, it can be confirmed that the compound represented by chemical formula 1 according to the present invention shows excellent characteristics in terms of driving voltage and efficiency when used in an organic light emitting device.

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,

r1 to R16 are the same as or different from each other, and each independently is hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring, and

at least one of R1 to R11 and R14 to R16 is represented by the following chemical formula 2,

chemical formula 2

In the chemical formula 2,

l1 and L2 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

ar1 and Ar2 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

when any one of R1 to R8 is represented by chemical formula 2, R4 or R5 combines with R to form a substituted or unsubstituted ring, and

indicates the position of binding to R1 to R11 and R14 to R16.

2. The compound according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 2-1:

chemical formula 2-1

In the chemical formula 2-1, L1, L2 and Ar2 are defined as in chemical formula 2, and

ar3 and Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

3. The compound 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,

g1 to G3 and G5 to G16 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to each other to form a substituted or unsubstituted ring, and

at least one of G1 to G3, G5 to G11, and G14 to G16 is represented by the chemical formula 2.

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

chemical formula 1-2

In the chemical formula 1-2,

y1 to Y16 are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,

at least one of Y9 to Y11 and Y14 to Y16 is represented by the chemical formula 2.

5. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 3-1 to 3-7:

chemical formula 3-1

Chemical formula 3-2

Chemical formula 3-3

Chemical formula 3-4

Chemical formula 3-5

Chemical formula 3-6

Chemical formula 3-7

In the chemical formulas 3-1 to 3-7, R1 to R3 and R5 to R16 are defined as in chemical formula 1, and L1, L2, Ar1 and Ar2 are defined as in chemical formula 2.

6. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 4-1 to 4-3:

chemical formula 4-1

Chemical formula 4-2

Chemical formula 4-3

In the chemical formulas 4-1 to 4-3, R1 to R16 are defined as in chemical formula 1, and L1, L2, Ar1 and Ar2 are defined as in chemical formula 2.

7. The compound of claim 1, wherein said L1 and L2 are the same or different from each other and each is independently a direct bond or a phenylene group.

8. The compound of claim 1, wherein said Ar1 is a substituted or unsubstituted fluorenyl group and said Ar2 is a substituted or unsubstituted aryl group.

9. The compound of claim 1, wherein Ar1 and Ar2 are dimethylfluorenyl.

10. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following structural formulae:

11. an organic light emitting device, comprising: a first electrode, a second electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers comprises the compound of any one of claims 1 to 10.

12. The organic light-emitting device according to claim 11, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.

13. An organic light-emitting device according to claim 11 wherein the organic layer comprises a light-emission-assisting layer and the light-emission-assisting layer comprises the compound.