Amine compound and organic light emitting device including the same

文档序号：957807 发布日期：2020-10-30 浏览：24次中文

阅读说明：本技术 胺化合物和包含其的有机发光器件 (Amine compound and organic light emitting device including the same ) 是由金旼俊金公谦金炯锡李敏宇于 2019-04-05 设计创作，主要内容包括：本申请涉及式1的化合物和包含其的有机发光器件。(The present application relates to a compound of formula 1 and an organic light emitting device comprising the same.)

1. A compound represented by the following formula 1:

[ formula 1]

In the formula 1, the first and second groups,

ar11 to Ar15 are the same or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or is bonded to an adjacent substituent to form a substituted or unsubstituted ring,

l and L2 to L5 are the same or different from each other and each independently is a direct bond; or a substituted or unsubstituted arylene group,

r1 is hydrogen; deuterium; a halogen group; a nitrile group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group, and is bonded to an adjacent substituent to form a substituted or unsubstituted ring,

r1 is an integer of 0 to 8, and when R1 is 2 or more, R1 are the same as or different from each other,

n is an integer of 1 to 3, and when n is 2 or 3, L are the same as or different from each other.

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

[ formula 2]

In formula 2, definitions of Ar11 to Ar15, L, L2 to L5, R1, R1, and n are the same as those defined in formula 1.

3. The compound of claim 1, wherein formula 1 is represented by any one of formulae 301 to 303 below:

[ formula 301]

[ formula 302]

[ formula 303]

In the formulae 301 to 303, the first and second formulae,

the definitions of L2 to L5 and Ar11 to Ar14 are the same as those defined in formula 1,

ar21 is substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,

r21 and R22 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; substituted or unsubstituted alkyl; substituted or unsubstituted haloalkyl; substituted or unsubstituted silyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,

k1 and k2 are 0 or 1,

r21 and r22 are integers from 0 to 6,

when R21 is 2 or more, R21 are the same as or different from each other, an

When R22 is 2 or more, R22 are the same as or different from each other.

4. The compound of claim 1, wherein Ar11 to Ar14 are the same or different from each other and are each independently an aryl group that is unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, a halogen group, a nitrile group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a silyl group, and a cycloalkyl group; or heteroaryl unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, haloalkoxy groups, silyl groups, and cycloalkyl groups.

5. The compound according to claim 1, wherein- (L) n-Ar15 in formula 1 is phenyl unsubstituted or substituted with deuterium, a halogen group, a nitrile group, an alkyl unsubstituted or substituted with deuterium, an alkoxy group, or a silyl group; or biphenyl unsubstituted or substituted with deuterium, a halogen group, a nitrile group, an alkyl unsubstituted or substituted with deuterium, an alkoxy group, or a silyl group.

6. The compound of claim 1, wherein aR15 is bonded to the adjacent R1 to form an unsubstituted or substituted deuterium, halogen, nitrile, methyl, isopropyl, tert-butyl, methoxy, CD₃Phenyl, phenyl substituted with deuterium, phenyl substituted with a halogen group, phenyl substituted with a nitrile group, or phenyl substituted with methyl; or a naphthalene ring.

7. The compound of claim 1, wherein formula 1 is any one of the following compounds:

8. an organic light emitting device comprising:

a first electrode;

a second electrode disposed to face the first electrode; and

an organic material layer having one or two or more layers disposed between the first electrode and the second electrode,

wherein one or more layers of the organic material layer comprise a compound according to any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound.

10. The organic light-emitting device according to claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound as a dopant of the light-emitting layer.

11. The organic light-emitting device according to claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound and a compound represented by the following formula H:

[ formula H ]

In the formula (H), the compound represented by the formula (I),

l21 and L22 are the same or different from each other and are each independently a direct bond; substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene group,

r31 to R38 are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl, and

ar101 and Ar102 are the same or different from each other and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl.

Technical Field

This application claims priority and benefit to korean patent application No. 10-2018-0039620, filed on 5.4.2018 to the korean intellectual property office, the entire contents of which are incorporated herein by reference.

The present specification relates to amine compounds and organic light emitting devices including the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween. Here, the organic material layer has a multi-layered structure composed of different materials in many cases to improve efficiency and stability of the organic light emitting device, and for example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic material layer, electrons are injected from a negative electrode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to a ground state again.

There is a continuing need to develop new materials for the aforementioned organic light emitting devices.

Disclosure of Invention

Technical problem

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

Technical scheme

An exemplary embodiment of the present specification provides a compound represented by the following formula 1.

[ formula 1]

In the formula 1, the first and second groups,

l and L2 to L5 are the same or different from each other and each independently is a direct bond; or a substituted or unsubstituted arylene group,

r1 is an integer of 0 to 8, and when R1 is 2 or more, R1 are the same as or different from each other, and

n is an integer of 1 to 3, and when n is 2 or 3, L are the same as or different from each other.

Further, an exemplary embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein the one or more layers of the organic material layer include the compound represented by formula 1.

Advantageous effects

The compound according to one exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and efficiency, low driving voltage, and/or improved lifespan characteristics may be improved in the organic light emitting device by using the compound.

Drawings

Fig. 1 to 4 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.

[ description of reference numerals ]

1: substrate

2: positive electrode

3: luminescent layer

4: negative electrode

5: hole injection layer

6: hole transport layer

7: electron injection and transport layer

8: electron blocking layer

9: hole blocking layer

Detailed Description

Hereinafter, the present specification will be described in more detail.

An exemplary embodiment of the present specification provides a compound represented by formula 1.

The compound represented by formula 1 has a structure in which two arylamine groups or arylheteroarylamine groups are linked to a core structure of benzocarbazole. When the compound of formula 1 is used as a dopant of a blue light emitting layer, the color purity of the device is improved, and long lifetime, high efficiency, and low voltage characteristics are exhibited.

In this specification, unless specifically described otherwise, when a portion "includes" one constituent element, this does not mean that another constituent element is excluded, but means that another constituent element may also be included.

In this specification, when one member is provided "on" another member, this includes not only a case where one member is in contact with another member but also a case where another member is present between two members.

In the context of the present specification,

or means a connected moiety.

Examples of the substituent in the present specification will be described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and a position to be substituted is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more are substituted, two or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from: hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; an alkyl group; a cycloalkyl group; a haloalkyl group; an alkoxy group; a haloalkoxy group; an aryloxy group; an aryl group; and a heterocyclic group, which is substituted with a substituent in which two or more substituents among the exemplified substituents are linked, or has no substituent. For example, the "substituent group to which two or more substituent groups are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the case where two or more substituents are linked means that hydrogen of any substituent is linked to another substituent. For example, isopropyl may be linked to phenyl to becomeOr

A substituent of (1).

In this specification, the case where three substituents are linked includes not only the case where (substituent 1) - (substituent 2) - (substituent 3) are sequentially linked to each other but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, two phenyl groups may be linked to an isopropyl group to becomeOr

A substituent of (1). This also applies to the case where four or more substituents are linked.

In the present specification, the halogen group may be F, Cl, I, etc., and is preferably F.

In the present specification, the silyl group may be an alkylsilyl group; or an arylsilyl group. The silyl group may be represented by SiRaRbRc, and Ra to Rc may be hydrogen, alkyl, or aryl.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30; 1 to 10; or 1 to 5. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms; or 3 to 13 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

In the present specification, a haloalkyl group may be straight-chain or branched, and means a group in which a hydrogen of the above alkyl group is substituted with one or two or more halogen groups. The number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. The description about the above alkyl group can be applied to the alkyl group. Specific examples of the haloalkyl group include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, isopropyloxy group, n-butoxy group, isobutoxy group, t-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3-dimethylbutyloxy group, 2-ethylbutoxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group and the like, but are not limited thereto.

In the present specification, a haloalkoxy group is a group in which a haloalkyl group is bonded to an oxygen atom, and the description about the above haloalkyl group can be applied to a haloalkyl group. The number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group include naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, perylene, and the like,A phenyl group, a fluorenyl group, and the like, but are not limited thereto.

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

When the fluorenyl group is substituted, the substituent may be

And the like. However, the substituent is not limited thereto.

In the present specification, the aryl group in the aryloxy group, the N-arylalkylamino group and the N-arylheteroarylamino group is the same as the above-mentioned example of the aryl group. Specific examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3, 5-dimethyl-phenoxy group, 2,4, 6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyloxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthrenyloxy group, 3-phenanthrenyloxy group, 9-phenanthrenyloxy group and the like.

In the present specification, a heteroaryl group contains one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinylAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzopyrrolyl, indolyl, benzothienyl, dibenzothienyl, benzofuranyl, benzoquinolinyl, benzonaphthothienyl, benzonaphthofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,Oxadiazolyl, thiadiazolyl, benzothiazolyl, thiophenylOxazinyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited to Here, the process is repeated.

In the present specification, the above examples of aryl groups may be applied to arylene groups, except that arylene groups are divalent.

In this specification, the above examples of heteroaryl groups may be applied to heteroarylene groups, with the difference that the heteroarylene group is divalent.

According to an exemplary embodiment of the present description, L and L2 to L5 are the same as or different from each other and are each independently selected from the group consisting of a direct bond, phenylene, biphenylene, terphenylene, tetrabiphenylene, naphthylene, anthracenylene, fluorenylene, phenanthrenylene, pyrenylene, and triphenylene (triphenylylene), which are unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, L and L2 to L5 are the same or different from each other and may each be independently selected from a direct bond or the following structural formula.

R and R' are alkyl or aryl. For example, R and R' are methyl or phenyl.

According to an exemplary embodiment of the present specification, L and L2 to L5 are the same as or different from each other, and each is independently a direct bond, phenylene, or biphenylene.

According to an exemplary embodiment of the present description, L and L2 to L5 are the same as or different from each other, and each is independently a direct bond, or a phenylene group.

According to an exemplary embodiment of the present specification, L and L2 to L5 are the same as or different from each other, and each is independently a direct bond, p-phenylene, or m-phenylene.

According to an exemplary embodiment of the present description, L and L2 to L5 are direct bonds.

According to an exemplary embodiment of the present description, L is a direct bond.

According to an exemplary embodiment of the present description, L2 to L5 are the same as or different from each other, and each is independently a direct bond, or a phenylene group.

According to one exemplary embodiment of the present description, Ar11 to Ar14 are the same or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl.

According to one exemplary embodiment of the present description, Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to one exemplary embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, a halogen group, a nitrile group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a silyl group, and a cycloalkyl group; or heteroaryl unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, haloalkoxy groups, silyl groups, and cycloalkyl groups.

In an exemplary embodiment of the present specification, when any one of Ar11 to Ar14 is an aryl group, the aryl group is a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, or a benzofluorenyl group.

In one exemplary embodiment of the present description, when any one of Ar11 to Ar14 is heteroaryl, the heteroaryl is dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, or naphthobenzothiophenyl.

In one exemplary embodiment of the present specification, when any one of Ar11 to Ar14 is a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a nitrile group, an unsubstituted or deuterium-substituted alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a silyl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms.

In an exemplary embodiment of the present description, when any one of Ar11 through Ar14 is a substituted aryl group, the substituent of the aryl group is deuterium, a halogen group, a nitrile group, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF ₃Trimethylsilyl, triphenylsilyl, or cyclohexyl.

In one exemplary embodiment of the present specification, when any one of Ar11 through Ar14 is a substituted heteroaryl group, the substituent of the heteroaryl group is deuterium, a halogen group, a nitrile group, an unsubstituted or deuterium-substituted alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a silyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an unsubstituted or deuterium-substituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present description, when any one of Ar11 through Ar14 is a substituted heteroaryl, the substituent of the heteroaryl is deuterium, a halogen group, a nitrile group, methyl, ethyl, propyl, isopropyl, t-butyl, CD, or a salt thereof₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, terphenyl, deuterium-substituted phenyl, deuterium-substituted biphenyl, deuterium-substituted naphthyl, or deuterium-substituted terphenyl.

In an exemplary embodiment of the present specification, Ar11 to Ar14 are the same or different from each other and are each independently unsubstituted or deuterated, haloAn element group, a nitrile group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a CD₃Trifluoromethyl, OCF₃Phenyl substituted with methoxy, ethoxy, trimethylsilyl, triphenylsilyl or cyclohexyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl, or cyclohexyl substituted biphenyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl, or cyclohexyl substituted naphthyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl or cyclohexyl-substituted fluorenyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD ₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl or cyclohexyl-substituted benzofluorenyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, or phenyl-substituted dibenzofuranyl substituted with deuterium; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl or cyclohexyl substituted naphthobenzofuranyl; unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl, phenyl, biphenyl, and the like,Naphthyl or dibenzothienyl substituted with deuterium-substituted phenyl; or unsubstituted or substituted by deuterium, halogen groups, nitrile groups, methyl, ethyl, propyl, isopropyl, tert-butyl, CD ₃Trifluoromethyl, methoxy, ethoxy, OCF₃Trimethylsilyl, triphenylsilyl or cyclohexyl substituted naphthobenzothienyl.

In an exemplary embodiment of the present description, Ar11 to Ar14 are the same or different from each other and are each independently unsubstituted or deuterated, halogen group, nitrile group, methyl group, isopropyl group, tert-butyl group, CD₃Trifluoromethyl, OCF₃Methoxy or trimethylsilyl substituted phenyl; a biphenyl group; a naphthyl group; a dimethyl fluorenyl group; a dimethylbenzofluorenyl group; unsubstituted or with deuterium, methyl, isopropyl, tert-butyl, CD₃Trimethylsilyl, phenyl or phenyl-substituted dibenzofuranyl substituted with deuterium; naphthobenzofuranyl; unsubstituted or with deuterium, methyl, isopropyl, tert-butyl, CD₃Trimethylsilyl, phenyl or dibenzothienyl substituted with deuterium-substituted phenyl; or naphthobenzothienyl.

According to an exemplary embodiment of the present specification, -N (-L2-Ar11) (-L3-Ar12) and-N (-L4-Ar13) (-L5-Ar14) of formula 1 are identical to each other.

According to an exemplary embodiment of the present specification, - (L) n-Ar15 in formula 1 is a phenyl group unsubstituted or substituted with deuterium, a halogen group, a nitrile group, an alkyl group unsubstituted or substituted with deuterium, an alkoxy group, or a silyl group; or biphenyl unsubstituted or substituted with deuterium, a halogen group, a nitrile group, an alkyl unsubstituted or substituted with deuterium, an alkoxy group, or a silyl group.

In one exemplary embodiment of the present description, Ar15 is a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, or is bonded to an adjacent group to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present description, Ar15 is bonded to adjacent R1 to form a substituted or unsubstituted aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, Ar15 is bonded to adjacent R1 to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

In one exemplary embodiment of the present specification, Ar15 is bonded to adjacent R1 to form a benzene ring that is unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, silyl groups, and cycloalkyl groups; or a naphthalene ring which is unsubstituted or substituted with a substituent selected from one of the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, silyl groups, and cycloalkyl groups.

In an exemplary embodiment of the present description, Ar15 is bonded to adjacent R1 to form an unsubstituted or deuterated or halogen group, a nitrile group, a methyl group, an isopropyl group, a tert-butyl group, a methoxy group, a CD₃Phenyl, phenyl substituted with deuterium, phenyl substituted with a halogen group, phenyl substituted with a nitrile group, or phenyl substituted with methyl; or a naphthalene ring.

In one exemplary embodiment of the present description, Ar15 is a substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl.

According to one exemplary embodiment of the present description, Ar15 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one exemplary embodiment of the present description, Ar15 is a substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl.

According to an exemplary embodiment of the present description, Ar15 is an aryl group unsubstituted or substituted with one substituent selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, silyl groups, and cycloalkyl groups.

In an exemplary embodiment of the present description, Ar15 is unsubstituted or deuterated, halogen group, nitrile group, methyl, ethyl, propyl, isopropyl, tert-butyl, CD₃Trifluoromethyl, methoxy, ethoxy, trimethylsilyl, triphenylsilyl or cyclohexyl substituted phenyl; a biphenyl group; or a naphthyl group.

In one exemplary embodiment of the present description, R1 is hydrogen or deuterium, or is bonded to adjacent Ar15 to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R1 is hydrogen or deuterium, or is bonded to adjacent Ar15 to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

In an exemplary embodiment of the present description, r1 is 0.

In an exemplary embodiment of the present description, r1 is 1.

In an exemplary embodiment of the present specification, formula 1 is represented by formula 2 below.

[ formula 2]

In formula 2, definitions of Ar11 to Ar15, L, L2 to L5, R1, R1, and n are the same as those defined in formula 1.

In an exemplary embodiment of the present specification, formula 1 is represented by any one of the following formulae 301 to 303.

[ formula 301]

[ formula 302]

[ formula 303]

In the formulae 301 to 303, the first and second formulae,

the definitions of L2 to L5 and Ar11 to Ar14 are the same as those defined in formula 1,

ar21 is substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,

k1 and k2 are 0 or 1,

r21 and r22 are integers from 0 to 6,

when R21 is 2 or more, R21 are the same as or different from each other, an

When R22 is 2 or more, R22 are the same as or different from each other.

In an exemplary embodiment of the present description, when k1 or k2 is 1, the naphthalene ring is fused to the benzocarbazole.

In one exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each is independently one substituent selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, haloalkyl groups, alkoxy groups, silyl groups, and cycloalkyl groups.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each is independently deuterium, a halogen group, a nitrile group, methyl, isopropyl, tert-butyl, methoxy, CD, or a salt thereof₃Phenyl, phenyl substituted with deuterium, phenyl substituted with a halogen group, phenyl substituted with a nitrile group, or phenyl substituted with a methyl group.

In an exemplary embodiment of the present specification, formula 301 is represented by formula 401 below.

[ formula 401]

In formula 401, definitions of Ar21, L2 to L5, and Ar11 to Ar14 are the same as those defined in formula 301.

In an exemplary embodiment of the present description, formula 302 is represented by formula 402 below.

[ formula 402]

In formula 402, R21, R21, k1, L2 to L5, and Ar11 to Ar14 are defined as those defined in formula 302.

In an exemplary embodiment of the present description, formula 303 is represented by formula 403 below.

[ formula 403]

In formula 403, R22, R22, k2, L2 to L5, and Ar11 to Ar14 are defined as those defined in formula 303.

According to one exemplary embodiment of the present specification, formula 1 may be any one selected from the following compounds.

According to an exemplary embodiment of the present specification, the full width at half maximum of the compound of formula 1 is 40nm or less. More preferably, the full width at half maximum is 30nm or less. When the full width at half maximum is in the above range, the color purity of blue light emission is improved.

The fluorescence intensity and maximum emission peak can be measured at room temperature (300K) by: the compound to be measured was dissolved in toluene as a solvent at a concentration of 1 μ M to prepare a sample for measuring fluorescence, and the sample solution was put into a quartz cell, followed by using a fluorescence measuring device (JASCO FP-8600 fluorescence spectrophotometer). In this case, in the fluorescence spectrum, the x-axis is the wavelength (λ, unit: nm), the y-axis is the luminosity, and the spread width of the peak at the height of 1/2 which is the height of the maximum emission peak refers to the full width at half maximum.

The compounds according to one exemplary embodiment of the present specification may be prepared by the preparation methods described below. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, and the like may be changed based on techniques known in the art.

For example, the core structure of the compound represented by formula 1 may be prepared as in the following general formulae 1 to 3. The substituents may be bonded by a method known in the art, and the kind or position of the substituent or the number of the substituent may be changed according to a technique known in the art. The substituents may be bonded as in the following general formulae 1 to 3, but the bonding method is not limited thereto.

[ general formula 1]

[ general formula 2]

[ general formula 3]

In the general formulae 1 to 3, the definitions of Ar11 to Ar15 are the same as those defined in formula 1. In the general formulae 1 to 3, L and L2 to L5 are not shown, but when a reactant in which L and L2 to L5 are substituted is used, a desired compound can be obtained.

An exemplary embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the above compound.

According to one exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be composed of a single layer structure, but may be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light emitting device is not limited thereto, and fewer or more organic layers may be included.

In the present specification, "layer" has a common meaning with "film" generally used in the art, and means a coating layer covering a target area. The size of the "layers" is not limited, and the sizes of the respective "layers" may be the same as or different from each other. In an exemplary embodiment, the size of the "layer" may be the same as the size of the entire device, may correspond to the size of a specific functional region, and may also be as small as a single sub-pixel.

In the present specification, the meaning that a specific a material is contained in the B layer includes both of the following: i) the fact that one or more a materials are contained in one B layer; and ii) the fact that the B layer is composed of one or more layers, and the A material is contained in one or more of the B layers of the plurality of layers.

In this specification, the meaning that a specific a material is contained in the C layer or the D layer includes all of the following: i) the fact that the a material is contained in one or more layers of the C layer having one or more layers; ii) the fact that the A material is contained in one or more layers of the D layer having one or more layers; and iii) the fact that the A material is contained in each of the C layer having one or more layers and the D layer having one or more layers.

For example, the structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 to 4, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which a positive electrode 2, a light emitting layer 3, and a negative electrode 4 are sequentially stacked on a substrate 1. Fig. 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include other organic material layers. In the above structure, the compound of formula 1 may be contained in the light emitting layer.

Fig. 2 illustrates a structure of an organic light emitting device in which a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7, and a negative electrode 4 are sequentially stacked on a substrate 1. Fig. 2 is an exemplary structure according to an exemplary embodiment of the present description, and may further include other organic material layers. Here, the compound of formula 1 may be contained in a hole injection layer, a hole transport layer, a light emitting layer, or an electron injection and transport layer.

Fig. 3 illustrates a structure of an organic light emitting device in which a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, an electron injection and transport layer 7, and a negative electrode 4 are sequentially stacked on a substrate 1. Fig. 3 is an exemplary structure according to an exemplary embodiment of the present description, and may further include other organic material layers. Here, the compound of formula 1 may be contained in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, or an electron injection and transport layer.

Fig. 4 illustrates a structure of an organic light emitting device in which a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 8, a light emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 7, and a negative electrode 4 are sequentially stacked on a substrate 1. Fig. 4 is an exemplary structure according to an exemplary embodiment of the present description, and may further include other organic material layers. Here, the compound of formula 1 may be contained in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, or an electron injection and transport layer.

According to one exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes a compound represented by formula 1.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by formula 1.

An organic light emitting device according to one exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by formula 1 and a compound represented by formula H below.

[ formula H ]

In the formula (H), the compound represented by the formula (I),

l21 and L22 are the same or different from each other and are each independently a direct bond; substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene group,

ar101 and Ar102 are the same or different from each other and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl.

In an exemplary embodiment of the present specification, L21 and L22 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and comprising N, O or S.

In an exemplary embodiment of the present specification, L21 and L22 are the same or different from each other and are each independently a direct bond; substituted or unsubstituted phenylene; substituted or unsubstituted naphthylene; or a substituted or unsubstituted thienylene group.

In one exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

In an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other and each independently is a substituted or unsubstituted monocyclic to tetracyclic aryl group; or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl.

In an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted phenalkenyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted benzofluorenyl; substituted or unsubstituted furyl; substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl group; substituted or unsubstituted dibenzothienyl; or a substituted or unsubstituted naphthobenzothienyl group.

In one exemplary embodiment of the present description, R31 to R38 are hydrogen.

In one exemplary embodiment of the present specification, formula H is any one selected from the following compounds.

In one exemplary embodiment of the present specification, the content of the compound represented by formula 1 is 0.01 to 30 parts by weight, based on 100 parts by weight of the compound represented by formula H; 0.1 to 20 parts by weight; or 0.5 to 10 parts by weight.

In one exemplary embodiment of the present specification, the light emitting layer may include a host material in addition to the compound represented by formula H. In this case, examples of the host material (mixed host compound) further contained include a fused aromatic ring derivative, a heterocyclic ring-containing compound, and the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and specific examples of the heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples are not limited thereto.

The weight ratio of the compound represented by formula H to the host compound mixed is 95:5 to 5:95, more preferably 30:70 to 70: 30.

In one exemplary embodiment of the present specification, the light emitting layer includes one or two or more compounds represented by formula H.

In one exemplary embodiment of the present specification, the light emitting layer including the compound represented by formula 1 and the compound represented by formula H exhibits blue color.

An organic light emitting device according to one exemplary embodiment of the present specification includes a light emitting layer having two or more layers, and at least one of the light emitting layer having two or more layers includes a compound represented by formula 1 and a compound represented by formula H. The light emitting layer including the compound represented by formula 1 and the compound represented by formula H exhibits blue color, and the light emitting layer not including the compound represented by formula 1 and the compound represented by formula H may include blue, red, or green light emitting compounds known in the art.

According to one exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the hole blocking layer, the electron transport layer, the electron injection layer, or the electron injection and transport layer includes a compound represented by formula 1.

According to an exemplary embodiment of the present description, the organic material layer may further include one or more layers selected from the group consisting of: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

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

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by: a metal, or a metal oxide having conductivity, or an alloy thereof is deposited on a substrate by using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation to form a first electrode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and then a material that can be used as a second electrode is deposited on the organic material layer. In addition to the above method, the organic light emitting device may be fabricated by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

In addition, in manufacturing an organic light emitting device, the compound represented by formula 1 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

According to one exemplary embodiment of the present description, the first electrode is a positive electrode and the second electrode is a negative electrode.

According to another exemplary embodiment of the present description, the first electrode is a negative electrode and the second electrode is a positive electrode.

As the positive electrode material, it is preferable to generally use a material having a high work function to facilitate hole injection into the organic material layer. Specific examples of positive electrode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO₂Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.

As the negative electrode material, it is preferable to generally use a material having a low work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO₂Al and Mg/Ag; and the like, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound of: it has the ability to transport holes and thus has the effect of injecting holes at the positive electrode and the excellent effect of injecting holes into the light emitting layer or the light emitting material, prevents excitons generated from the light emitting layer from moving to the electron injecting layer or the electron injecting material, and is also excellent in the ability to form a thin film. The Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanenitrile-based hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.

In one exemplary embodiment of the present specification, in the hole injection layer, the arylamine-based organic material is doped with a hexanitrile hexaazatriphenylene-based organic material.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material having high hole mobility that can receive holes from the positive electrode or the hole injection layer and transport the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like, but are not limited thereto.

The light-emitting material used for the light-emitting layer is a material that can emit light in the visible light region by receiving and combining holes and electrons from the hole-transport layer and the electron-transport layer, respectively, and is preferably a material having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzeneOxazole, benzothiazole-based and benzimidazole-based compounds; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; a polyfluorene; rubrene; and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. Examples of the host material include a fused aromatic ring derivative or a heterocyclic ring-containing compound and the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples thereof are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, having an arylamino group,

Diindenoperene (periflanthene), etc., a styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material having high electron mobility that can proficiently receive electrons from the negative electrode and transfer the electrons to the light emitting layer. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq₃The complex of (1); an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials having a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: with transmission of electronsThe ability of (a), the effect of injecting electrons from the negative electrode, the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, the prevention of excitons generated from the light-emitting layer from moving to the hole-injecting layer, and the ability of forming a thin film are also excellent. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,

Azole,Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

In one exemplary embodiment of the present specification, the electron injection and transport layer includes an alkali metal complex compound.

The electron blocking layer is a layer that can improve the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks holes from reaching the negative electrode, and may be generally formed under the same conditions as those of the electron injection layer. Specific examples thereof includeOxadiazole derivativesBiological or triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type, depending on the material used.

EMBODIMENTS FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail with reference to examples, comparative examples, and the like for specifically describing the present specification. However, the embodiments and comparative examples according to the present specification may be modified into various forms, and should not be construed that the scope of the present specification is limited to the embodiments and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully illustrate the present specification to those of ordinary skill in the art.

< Synthesis example >

Synthesis of intermediates

1. Synthesis of intermediates of formula 1

1) Preparation of Compound a-2

200.0g (1.0 eq) of 7-chloronaphthalen-2-amine, 443.25g (1.0 eq) of 1-bromo-4-chloro-2-iodobenzene, 201.3g (1.5 eq) of NaOtBu, 3.13g (0.01 eq) of Pd (OAc)₂And 8.08g (0.01 eq) of 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene dissolved in 4L of 1, 4-bis In an alkane, the resulting solution was stirred under reflux. After 3 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resultant was completely dissolved in ethyl acetate, the resultant solution was washed with water, and 70% of the solvent was removed again by reduced pressure. Next, hexane was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 283.41g (yield 61%) of compound a-2. [ M + H ]]＝333

2) Preparation of Compound a-1

283.41g (1.0 equivalent)) Compound a-2, 3.90g (0.01 eq) Pd (t-Bu)₃P)₂And 212.21g (2.50 eq.) K₂CO₃The mixture was taken up in 2L of dimethylacetamide and the resulting mixture was stirred under reflux. After 3 hours, crystals were precipitated by pouring the reaction into water and filtered. After the filtered solid was completely dissolved in 1, 2-dichlorobenzene, the resulting solution was washed with water, crystals were precipitated by concentrating the solution having the product dissolved therein under reduced pressure, cooled, and then filtered. The product was purified by column chromatography to obtain 74.97g (yield 39%) of the compound a-13, 8-dichloro-5H-benzo [ b ]]Carbazole. [ M + H ]]＝252

2. Synthesis of intermediates of formula 3

1) Synthesis of intermediate A-2

40g of 2-bromo-7-methoxynaphthalene, 40g of intermediate A-1, 110g of cesium carbonate and 0.86g of [ bis (tri (tert-butyl) phosphine) palladium (0)]Pd(P^tBu₃)₂After being placed in 1.2L of xylene, the resulting mixture was heated and stirred at 150 ℃ for 5 hours. After the reaction was terminated, the reaction solution was cooled to room temperature by adding water and NH thereto₄The Cl solution was aliquoted by addition of MgSO 2₄(anhydrous) treatment for filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/acetonitrile) to obtain 52g of intermediate a-2. [ M + H ]]＝388

2) Synthesis of intermediate A-3

45g of intermediate A-2, 22g of sodium tert-butoxide and 1.2g of [ bis (tri (tert-butyl) phosphine) palladium (0)]Pd(P^tBu₃)₂After being placed in 500mL of dimethylacetamide, the resulting mixture was heated and stirred at 120 ℃ for 10 hours. After the reaction was terminated, the reaction solution was cooled to room temperature by adding water and NH thereto₄The Cl solution was aliquoted by addition of MgSO 2₄(anhydrous) treatment for filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 22g of intermediate a-3. [ M + H ]]＝352

3) Synthesis of intermediate A-5

After 20g of intermediate A-3 and 23g of aluminum chloride were placed in 200mL of chlorobenzene under a nitrogen atmosphere, the resulting mixture was heated and stirred at 130 ℃ for 8 hours. After the reaction was terminated, the reaction solution was cooled to room temperature, aliquoted by adding water and ethyl acetate thereto, and then aliquoted by using MgSO ₄(anhydrous) treatment for filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethyl acetate/hexane) to obtain 15g of intermediate a-4.

After 300mL of dimethylformamide was put into 15g of intermediate A-4 and 32g of potassium carbonate, 17mL of nonfluoryl fluoride (nonafluorobutanesulfonyl fluoride) was added dropwise thereto at room temperature. After the reaction was terminated by stirring the resulting mixture for 5 hours, the reaction solution was filtered. The filtered solution was aliquoted by adding water and ethyl acetate thereto, then by using MgSO₄(anhydrous) treatment for filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 30g of intermediate a-5.

3. Synthesis of Compounds

Synthesis example 1

10.0g (1.0 equivalent) of the compound 1-1, 19.52g (2.2 equivalents) of bis ([1,1' -biphenyl)]-4-yl) amine, 0.14g (0.01 eq) Pd (t-Bu)₃P)₂And 6.63g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reducing the pressureAnd (3) preparing. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 16.72g (yield 65%) of compound 1. [ M + H ] ]＝933

Synthesis example 2

10.0g (1.0 equivalent) of the compound 2-1, 12.69g (2.2 equivalents) of N-phenyl-4- (trimethylsilyl) aniline, 0.12g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 5.74g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 12.57g (yield 61%) of compound 2. [ M + H ]]＝829

Synthesis example 3

10.0g (1.0 equiv.) of Compound 3-1, 12.74g (2.2 equiv.) of N- (phenyl-d 5) naphthalen-1-amine, 0.13g (0.01 equiv.) of Pd (t-Bu₃P)₂And 6.20g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 13.20g (yield 67%) of compound 3. [ M + H ] ]＝763

Synthesis example 4

10.0g (1.0 equivalent) of the compound 4-1, 15.22g (2.2 equivalents) of N- (3, 5-dimethylphenyl) dibenzo [ b, d ] was added]Thiophene-4-amine, 0.11g (0.01 eq) Pd (t-Bu)₃P)₂And 5.48g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 14.19g (yield 64%) of compound 4. [ M + H ]]＝973

Synthesis example 5

10.0g (1.0 equivalent) of the compound 5-1, 15.70g (2.2 equivalents) of N- (4-fluorophenyl) -6- (methyl-d 3) dibenzo [ b, d ] are added]Furan-4-amine, 0.12g (0.01 eq) Pd (t-Bu)₃P)₂And 5.82g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 13.50g (yield 60%) of compound 5. [ M + H ] ]＝929

Synthesis example 6

10g (1.0 equivalent) of Compound 6-1, 12.77g (2.2 equivalents) of 4- (tert-butyl) -N- (p-tolyl) aniline, 0.12g (0.01 eq) Pd (t-Bu)₃P)₂And 5.82g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 12.89g (yield 65%) of compound 6. [ M + H ]]＝819

Synthesis example 7

10.0g (1.0 equivalent) of the compound 7-1, 17.21g (2.2 equivalents) of N- (4-isopropylphenyl) - [1,1' -biphenyl]-4-amine, 0.14g (0.01 eq) Pd (t-Bu)₃P)₂And 6.54g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 15.38g (yield 65%) of compound 7. [ M + H ] ]＝870

Synthesis example 8

10.0g (1.0 equiv) of Compound 8-1, 20.48g (2.2 equiv) of N- ([1,1' -biphenylyl)]-3-yl]Dibenzo [ b, d ]]Furan-2-amine, 0.14g (0.01 eq) Pd (t-Bu)₃P)₂And 6.67g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 17.28g (yield 65%) of compound 8. [ M + H ]]＝959

Synthesis example 9

1.0g (1.0 equivalent) of the compound 9-1, 11.15g (2.2 equivalents) of N-phenylnaphthalen-2-amine, 0.12g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 5.56g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 12.33g (yield 61%) of compound 9. [ M + H ] ]＝875

Synthesis example 10

10.0g (1.0 equivalent) of the compound 10-1, 13.32g (2.2 equivalents) of N- (phenyl-d 5) dibenzo [ b, d]Furan-4-amine, 0.14g (0.01 eq) Pd (t-Bu)₃P)₂And 5.50g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 12.88g (yield 63%) of compound 10. [ M + H ]]＝893

Synthesis example 11

10.0g (1.0 equivalent) of Compound 11-1, 14.76g (2.2 equivalents) of N-phenyldibenzo [ b, d ]]Thiophene-1-amine, 0.12g (0.01 eq) Pd (t-Bu)₃P)₂And 5.85g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 14.07g (yield 65%) of compound 11. [ M + H ] ]＝889

Synthesis example 12

10.0g (1.0 equivalent) of Compound 12-1, 15.30g (2.2 equivalents) of 9, 9-dimethyl-N-phenyl-9H-fluoren-2-amine, 0.12g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 5.86g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 13.50g (yield 61%) of compound 12. [ M + H ]]＝909

Synthesis example 13

10.0g (1.0 equivalent) of the compound 13-1, 13.36g (2.2 equivalents) of N- (4-methoxyphenyl) naphthalen-2-amine, 0.12g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 586g (2.5 equivalents) of NaOtBu are placed in 250ml of xylene and the resulting mixture is stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 13.04g (yield 64%) of compound 13. [ M + H ] ]＝837

Synthesis example 14

10.0g (1.0 equivalent) of Compound 14-1, 11.00g (2.2 equivalents) of 3- (o-tolylamino) benzonitrile, 0.12g (0.01 equivalent) of Pd (t-Bu₃P)₂And 5.77g (2.5 equivalents) of NaOtBu in 250ml of xylene, and the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 11.13g (yield 61%) of compound 14. [ M + H ]]＝760

Synthesis example 15

17.18g (1.0 equivalent) of the compound 15-1, 5.79g (2.2 equivalents) of bis (4- (tert-butyl) phenyl) amine, 0.14g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 18.34g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolvedIn CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 14.45g (yield 67%) of compound 15. [ M + H ] ]＝891

Synthesis example 16

10.0g (1.0 equiv.) of Compound 16-1, 22.13g (2.2 equiv.) of N- (4- (tert-butyl) phenyl) -9, 9-dimethyl-9H-fluoren-2-amine, 0.17g (0.01 equiv.) of Pd (t-Bu)₃P)₂And 15.63g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 20.14g (yield 67%) of compound 16. [ M + H ]]＝1021

Synthesis example 17

10.0g (1.0 equivalent) of Compound 17-1, 16.28g (2.2 equivalents) of 2-methyl-N- (4- (trifluoromethyl) phenyl) aniline, 0.15g (0.01 equivalent) of Pd (t-Bu)₃P)₂And 15.63g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolvedIn CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 15.84g (yield 64%) of compound 17. [ M + H ] ]＝840

Synthesis example 18

10.0g (1.0 equivalent) of the compound 18-1, 18.23g (2.2 equivalents) of N- (3, 5-difluorophenyl) - [1,1' -biphenyl]-4-amine, 0.15g (0.01 eq) Pd (t-Bu)₃P)₂And 15.63g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 16.17g (yield 61%) of compound 18. [ M + H ]]＝900

Synthesis example 19

10.0g (1.0 equivalent) of Compound 19-1, 19.43g (2.2 equivalents) of N- (3- (trimethylsilyl) phenyl) dibenzo [ b, d ] is added]Thiophene-2-amine, 0.12g (0.01 eq) Pd (t-Bu)₃P)₂And 13.48g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the obtained product isThe product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 18.50g (yield 67%) of compound 19. [ M + H ] ]＝1087

Synthesis example 20

10.0g (1.0 equivalent) of the compound 20-1, 13.82g (2.2 equivalents) of N-phenyl- [1,1' -biphenyl]-4-amine, 0.13g (0.01 eq) Pd (t-Bu)₃P)₂And 13.59g (2.5 eq) K₃PO₄Put into a 250ml container

In an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 13.73g (yield 61%) of compound 20. [ M + H ]]＝880

Synthesis example 21

10.0g (1.0 equiv) of the compound 21-1, 21.14g (2.2 equiv) of N- ([1,1' -biphenylyl) are added]-3-yl) naphthalen-2-amine, 0.16g (0.01 eq) Pd (t-Bu)₃P)₂And 17.26g (2.5 eq) K₃PO₄Put into a 250ml containerIn an alkane, the resulting mixture was stirred under reflux. After 2 hours, when the reaction was terminated, the solvent was removed by reduced pressure. Thereafter, the resulting product was completely dissolved in CHCl₃The resulting solution was washed with water, and about 50% of the solvent was removed again by reduced pressure. Then, ethyl acetate was added thereto under reflux to precipitate crystals, which were then cooled and filtered. The resulting product was subjected to column chromatography to obtain 18.95g (yield 65%) of compound 21. [ M + H ] ]＝897

< Experimental example >

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