KR20170027250A - Amino fluorene polymer and organic light-emitting device including the same - Google Patents

Abstract

Provided are an amino fluorene polymer and an organic light-emitting device comprising the same. The amino fluorene polymer comprises a first repeating unit, represented by chemical formula 1. The organic light-emitting device using the amino fluorene polymer can improve light-emitting durability and current efficiency.

Description

[0001] The present invention relates to an aminofluorene polymer and an organic light-

Aminofluorene polymers and organic light emitting devices containing them are presented.

An organic light-emitting device is a self-light-emitting device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and being able to have multiple colors .

According to an example, the organic light emitting element may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transporting region may be provided between the anode and the light emitting layer, and an electron transporting region may be provided between the light emitting layer and the cathode. The holes injected from the anode move to the light emitting layer via the hole transporting region, and electrons injected from the cathode move to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

An aminofluorene polymer and an organic light emitting element employing the same.

According to an aspect, there is provided an aminofluorene polymer comprising a first repeating unit represented by the following formula (1): < EMI ID =

≪ Formula 1 >

In Formula 1,

R ₁ to R ₃ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group; ;

m1 is an integer from 1 to 20;

F and F 'are independently selected from a substituted or unsubstituted azafluorenylene group and a substituted or unsubstituted fluorenylene group;

n1 and n2 are independently selected from 1 and 2;

A is a group represented by the following formula (2);

R ₄ represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and _{-N (Q 1) (Q 2} ) ;

(2)

In Formula 2,

L ₁ and L ₂ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ A substituted or unsubstituted C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ oxycycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ oxyarylene group, a substituted or unsubstituted aryl group, a C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene _{group, -Si (Q 4) (Q} 5) - and -N (Q ₄₎ - is selected from;

n3 and n4 are independently from each other selected from 1 and 2;

Ar ₁ represents a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, An unsubstituted C ₅ -C ₃₀ heteroaryl group and -N (Q ₆ ) (Q ₇ );

Ar ₁ is optionally fused with F, F ', L ₁ or L ₂ to form a ring;

Q ₁ to Q ₇ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;

* Is the binding site with neighboring atoms.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode; Wherein the organic layer comprises the aminofluorene polymer described above.

The organic light emitting device employing the aminofluorene polymer improves the light emitting lifetime and current efficiency.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

In the present specification, "x to y" representing the range means "x to less than y.

Unless otherwise stated, the measurement of the operation and physical properties is carried out under the conditions of a temperature of 20 to 25 占 폚 and a humidity of 40 to 50%.

In order to manufacture a large-sized organic light emitting device at a lower cost, a solution coating method can be used. The solution coating method is advantageous in that the utilization efficiency of the material is higher than that of the vacuum vapor deposition method, a large-sized organic light emitting device can be easily manufactured, and a costly vacuum deposition apparatus is not required.

As the material used in the solution coating method, for example, there can be a low-molecular material and a high-molecular material. Among them, the polymer material has an advantage of high uniformity of application and easy formation of a laminate.

For example, the following Patent Documents 1 to 10 disclose a material for an organic light-emitting device in which a part of a low-molecular material is substituted with a vinyl group and polymerized to polymerize.

Patent Document 1: JP-A-7-90255

Patent Document 2: JP-A-8-54833

Patent Document 3: Japanese Patent Application Laid-Open No. 8-269133

Patent Document 4: JP-A No. 2001-098023

Patent Document 5: Japanese Patent Application Laid-Open No. 2002-110359

Patent Document 6: Japanese Patent Application Laid-Open No. 2003-313240

Patent Document 7: Japanese Patent Application Laid-Open No. 2004-059743

Patent Document 8: Japanese Patent Application Laid-Open No. 2006-237592

Patent Document 9: JP-A-2008-198989

Patent Document 10: Japanese Patent Application Laid-Open No. 2008-218983

However, the organic light emitting devices manufactured by the solution coating method using the materials for the organic light emitting devices disclosed in the above Patent Documents 1 to 10 have a problem that the light emission lifetime is not sufficient.

Hereinafter, embodiments of the present invention will be described. The present invention is not limited to the following embodiments.

Aminofluorene polymer

The aminofluorene polymer according to one embodiment of the present invention is a material for an organic light emitting device which can be formed by a solution coating method. The aminofluorene polymer has high solubility in solvents and high stability of the film formed after coating. In addition, the lifetime of the organic light emitting device including the aminofluorene polymer can be improved.

The aminofluorene polymer is a polymer formed by polymerizing a polymerizable monomer and may include a first repeating unit represented by the following formula (1)

≪ Formula 1 >

In Formula 1, R ₁ to R ₃ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, or a substituted or unsubstituted C ₆ -C ₃₀ aryl group; ≪ / RTI >

For example, in the above formula (1), R ₁ to R ₃ independently of each other may be selected from a hydrogen atom, a methyl group, an ethyl group, a n-propyl group and an n-butyl group, but are not limited thereto.

As another example, in the above formula (1), R ₁ to R ₃ may be independently selected from a hydrogen atom and a methyl group, but are not limited thereto.

M1 represents a repetition number of moieties represented by * -A- (F ') _n2 - *', and m1 may be an integer of 1 to 20.

For example, in formula (1), m1 may be an integer of 1 to 15, but is not limited thereto.

In Formula 1, F and F 'may be independently selected from substituted or unsubstituted azafluorenylene groups and substituted or unsubstituted fluorenylene groups.

For example, in the above formula (1), F and F 'independently of each other may be a group represented by the following formula (3), but are not limited thereto:

(3)

In Formula 3,

R ₅ to R ₈ are each independently a bond site, a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cyclo alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a C ₆ ring substituted with a substituted or unsubstituted -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and - N (Q ₁ ) (Q ₂ );

Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;

Two of R ₅ to R ₈ are a bonding site;

Q ₁ to Q ₃ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;

a and b are independently selected from 1, 2, 3 and 4;

Y ₁ to Y ₈ are, independently of each other, a carbon atom or a nitrogen atom.

For example, in Formula 3, R ₅ to R ₈ independently represent a bonding site, a hydrogen atom, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₃₀ aryl group, and a C ₅ -C ₃₀ heteroaryl group;

A C ₁ -C ₂₀ alkyl group substituted by at least one selected from a halogen atom and a C ₆ -C ₃₀ aryl group; And

A C ₃₀ aryl group and a C ₅ -C ₃₀ heteroaryl group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₃₀ aryl group, and a C ₆ -C ₃₀ aryl group substituted with a C ₁ -C ₂₀ alkyl group, An aryl group; ;

Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;

Two substituents out of R ₅ to R ₈ may be binding sites but are not limited thereto.

As another example, in the general formula (3), R ₅ to R ₈ independently represent a bonding site, a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, Butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, Methylpropyl group, 1-ethyl-3-isopropylpropyl group, 1-ethylbutyl group, Methylbutyl group, 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-octyl group, N-heptyl group, n-octyl group, n-octyl group, heptyl group, heptyl group, heptyl group, heptyl group, , n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group and n-eicosyl group oup), phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, pyrimidyl, pyrazinyl, triazinyl, furanyl and thiophenyl;

-F, a methyl group, an ethyl group and an n-propyl group substituted with at least one selected from a phenyl group and a naphthyl group; And

A phenyl group substituted with a methyl group and a tert-butyl group substituted with a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- A phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group and a thiophenyl group which are substituted with at least one selected from a phenyl group substituted with a butyl group; ;

Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;

Two substituents out of R ₅ to R ₈ may be binding sites but are not limited thereto.

As another example, in the general formula (3), R ₅ to R ₈ independently represent a bonding site, a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, A tert-butyl group, an n-octyl group, an n-octadecyl group, a phenyl group, a pyridinyl group and a thiophenyl group;

A methyl group and an ethyl group substituted with at least one selected from -F and a phenyl group; And

A phenyl group substituted with at least one selected from a methyl group, a tert-butyl group, an n-octyl group, a phenyl group and a phenyl group substituted with a tert-butyl group; ;

Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;

Two substituents out of R ₅ to R ₈ may be binding sites but are not limited thereto.

As another example, F and F 'in the above formula (1) may be independently selected from the groups represented by the following formulas (4-1) to (4-58), but are not limited thereto:

Of the above-mentioned formulas (4-1) to (4-58)

Two hydrogen atoms are replaced by binding sites.

In the above formula (1), n1 represents the number of repetitions of F, n2 represents the number of repetitions of F ', and n1 and n2 may be independently selected from 1 and 2.

In Formula 1, A may be a group represented by the following Formula 2:

(2)

In Formula 2,

L ₁ and L ₂ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ A substituted or unsubstituted C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ oxycycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ oxyarylene group, a substituted or unsubstituted aryl group, a C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene _{group, -Si (Q 4) (Q} 5) - and -N (Q ₄₎ - is selected from;

n3 and n4 are independently from each other selected from 1 and 2;

Ar ₁ represents a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, An unsubstituted C ₅ -C ₃₀ heteroaryl group and -N (Q ₆ ) (Q ₇ );

Ar ₁ is optionally fused with F, F ', L ₁ or L ₂ to form a ring;

Q ₄ to Q ₇ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;

* Is the binding site with neighboring atoms.

For example, in Formula 2, L ₁ and L ₂ independently represent a single bond, a C ₁ -C ₂₀ alkylene group, and a C ₆ -C ₃₀ arylene group; And

A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; , But is not limited thereto.

As another example, in Formula 2, L ₁ and L ₂ independently represent a single bond, a methylene group, and a phenylene group; And

A methylene group and a phenylene group substituted with at least one selected from a methyl group, an n-hexyl group and a phenyl group; , But is not limited thereto.

For example, in Formula 2, Ar ₁ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group, or a C ₆ -C ₃₀ aryl group; And

C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;

Ar ₁ may optionally form F, F ', L ₁ or L ₂ to form a ring, but is not limited thereto.

As another example, in the formula 2, Ar ₁ represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n- butyl group, an isobutyl group, Isopropyl group, 1,2-dimethylpropyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, Ethylbutyl, n-butyl, isobutyl, n-butyl, isobutyl, Methyl-1-isopropyl group, 1-tert-butyl-2-methyl-propyl group, phenyl group, naphthyl group, anthracenyl group, and phenan A threnyl group; And

A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; ;

Ar ₁ may optionally form F, F ', L ₁ or L ₂ to form a ring, but is not limited thereto.

As another example, in the general formula (2), Ar ₁ is selected from a hydrogen atom, a methyl group, a n-hexyl group, a phenyl group, a naphthyl group and a group represented by the following general formulas (8-1) to (8-6);

Ar ₁ can optionally be fused with F, F ', L ₁ or L ₂ to form a ring, but is not limited thereto:

Among the above-mentioned formulas (8-1) to

* Is the binding site with neighboring atoms.

Wherein R ₄ is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted Or a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryl oxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and -N (Q ₁ (Q < ₂ >);

Q ₁ to Q ₃ independently of each other may be selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group.

For example, in Formula 1, R ₄ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₃₀ aryl group, a C ₁ -C ₂₀ alkoxy group, and -N (Q ₁ ) (Q ₂ ); And

C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;

Q ₁ and Q ₂ are, independently of each other, a hydrogen atom, a C ₆ -C ₃₀ aryl group; And

A C ₆ -C ₃₀ aryl group substituted with at least one selected from C ₁ -C ₂₀ alkyl groups; , But is not limited thereto.

As another example, in the general formula (1), R ₄ represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, Isopropyl group, 1,2-dimethylpropyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, Ethylbutyl, n-butyl, isobutyl, n-butyl, isobutyl, Methyl-1-isopropyl group, 1-tert-butyl-2-methyl-propyl group, phenyl group, naphthyl group, anthracenyl group, phenanthrene group N-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-pentyloxy group, octanoic tilok group and _{-N (Q 1) (Q 2} ); And

A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; ;

Q ₁ and Q ₂ independently represent a hydrogen atom, a phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group; And

An ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group; A phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group substituted with at least one selected from the group consisting of a halogen atom, , But is not limited thereto.

As another example, in the above formula (1), R ₄ may be selected from a hydrogen atom, a methyl group, a n-hexyl group, a phenyl group, a naphthyl group, a methoxy group and groups represented by the following formulas (8-1) to (8-7) But are not limited to:

In the above formulas 8-1 to 8-7

* Is the binding site with neighboring atoms.

For example, the first repeating unit represented by the formula (1) may be represented by the following formula (1-1), but is not limited thereto:

<Formula 1-1 '

In Formula 1-1,

R ₁ to R ₃ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group; ;

m1 is an integer from 1 to 20;

F and F 'are independently selected from a substituted or unsubstituted azafluorenylene group and a substituted or unsubstituted fluorenylene group;

n1 and n2 are independently selected from 1 and 2;

A is a group represented by the following formula (2);

R ₄ represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and _{-N (Q 1) (Q 2} ) ;

(2)

In Formula 2,

L ₁ and L ₂ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ A substituted or unsubstituted C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ oxycycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ oxyarylene group, a substituted or unsubstituted aryl group, a C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene _{group, -Si (Q 4) (Q} 5) - and -N (Q ₄₎ - is selected from;

n3 and n4 are independently from each other selected from 1 and 2;

Ar ₁ represents a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, An unsubstituted C ₅ -C ₃₀ heteroaryl group and -N (Q ₆ ) (Q ₇ );

Ar ₁ is optionally fused with F, F ', L ₁ or L ₂ to form a ring;

* Is the binding site with neighboring atoms;

R ₅ to R ₈ independently represent a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted Or an unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and -N (Q is selected from ₁₎ (Q _2);

Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;

a and b are independently selected from 1, 2, 3 and 4;

Y ₁ to Y ₈ are, independently of each other, a carbon atom or a nitrogen atom;

Q ₁ to Q ₇ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group.

For example, the first repeating unit represented by Formula 1 may be selected from the following formulas, but is not limited thereto:

In the above formulas, m is an integer of 1 to 10.

The aminofluorene polymer has a fluorene structure directly bonded to the side chain of the polymer. Further, the fluorene structure is further substituted with a substituent containing i) an amine structure and ii) a substituent containing a fluorene structure. The amine structure may be continuously substituted, the fluorene structure may be substituted continuously, or the amine structure and the fluorene structure may be alternately substituted.

The organic light emitting device including the aminofluorene polymer according to an embodiment of the present invention can improve the lifetime of light emission and current efficiency.

The aminofluorene polymer comprising the first repeating unit represented by the above-mentioned formula (1) contains a fluoreneylene group in the polymerization site, and the dissociation energy of carbon-carbon bond is 3 times higher than that of the polymer having a phenylene group in the polymerization site . Therefore, the luminescent lifetime of the organic light emitting device including the same can be improved.

The number average molecular weight (Mn) of the aminofluorene polymer may be, for example, 10000 or more and 100000 or less, but is not limited thereto. When the above range is satisfied, the viscosity of the coating agent for forming the layer containing the aminofluorene polymer (for example, the hole injection layer and / or the hole transport layer) can be suitably controlled, Can be formed.

The weight average molecular weight (Mw) of the aminofluorene polymer may be, for example, 10000 or more and 300000 or less, but is not limited thereto. When the above range is satisfied, the viscosity of the coating agent for forming the layer containing the aminofluorene polymer (for example, the hole injection layer and / or the hole transport layer) can be suitably controlled, Can be formed.

The degree of dispersion (weight average molecular weight / number average molecular weight) of the aminofluorene polymer may be, for example, 1.5 or more and 2.5 or less, but is not limited thereto. When the above range is satisfied, the viscosity of the coating agent for forming the layer containing the aminofluorene polymer (for example, the hole injection layer and / or the hole transport layer) can be suitably controlled, Can be formed.

The method of measuring the number average molecular weight (Mn), the weight average molecular weight (Mw) and the degree of dispersion is not particularly limited and can be measured and calculated in accordance with a known method. In the present specification, the number average molecular weight (Mn), the weight average molecular weight (Mw) and the degree of dispersion adopt values measured in the following examples.

The aminofluorene polymer may further comprise a second repeating unit derived from a monomer containing at least one crosslinking group. That is, the aminofluorene polymer may be a copolymer including the first repeating unit and the second repeating unit together:

The crosslinking group may be represented by the following general formulas (5-1) to (5-10), but is not limited thereto:

Of the above formulas (5-1) to (5-10)

R ₁₀ to R ₁₆ are, independently from each other, a hydrogen atom or a substituted or unsubstituted C ₁ -C ₂₀ alkyl group;

p is an integer from 1 to 10;

* Is the binding site with neighboring atoms.

In one embodiment, the second repeating unit may be represented by the following general formula (6), but is not limited thereto:

(6)

In Formula 6,

R ₁₇ to R ₁₉ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, or a substituted or unsubstituted C ₆ -C ₃₀ aryl group,

R ₂₀ to R ₂₈ independently represent a crosslinking group, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group , A substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ A substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, -Si (Q ₁ ) is selected from (Q ₂₎ (Q _3), and _{-N (Q 1) (Q 2} );

Adjacent substituents of R ₂₀ to R ₂₈ are optionally bonded to each other to form a ring;

At least one of R ₂₀ to R ₂₈ is selected from the crosslinking groups represented by the following formulas (5-1) to (5-10);

c, d, e and f are independently of each other selected from 1, 2 and 3;

A 'is a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ aryloxy cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ aryl-oxy group, a substituted or unsubstituted C ₇ -C ₄₀ ahreu An alkylene group, a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group, -Si (Q ₄ ) (Q ₅ ) - and -N (Q ₄ ) -;

n5 is selected from 1, 2, 3, 4 and 5;

m2 is an integer from 0 to 20;

Q ₁ to Q ₅ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;

Of the above formulas (5-1) to (5-10)

R ₁₀ to R ₁₆ are, independently from each other, a hydrogen atom or a substituted or unsubstituted C ₁ -C ₂₀ alkyl group;

p is an integer from 1 to 10;

* Is the binding site with neighboring atoms.

For example, in the above formula (6), R ₁₇ to R ₁₉ independently of each other may be selected from a hydrogen atom, a methyl group, an ethyl group, a n-propyl group and an n-butyl group, but are not limited thereto.

As another example, in the above formula (6), R ₁₇ to R ₁₉ independently of each other may be selected from a hydrogen atom and a methyl group, but are not limited thereto.

For example, in the above formula (6), R ₂₀ to R ₂₈ independently represent a crosslinking group, a hydrogen atom, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₃₀ aryl A C ₁ -C ₂₀ alkoxy group and -N (Q ₁ ) (Q ₂ ); And

C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;

Adjacent substituents of R ₂₀ to R ₂₈ are optionally bonded to each other to form a ring;

At least one of R ₂₀ to R ₂₈ is selected from the crosslinking groups represented by the above formulas 5-1 to 5-10;

Q ₁ and Q ₂ are, independently of each other, a hydrogen atom, a C ₆ -C ₃₀ aryl group; And

A C ₆ -C ₃₀ aryl group substituted with at least one selected from C ₁ -C ₂₀ alkyl groups; , But is not limited thereto.

As another example, in the general formula (6), R ₂₀ to R ₂₈ independently represent a crosslinking group, a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group butyl group, n-butyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl Ethyl-3-methylbutyl group, an n-octyl group, a 2-ethylhexyl group, a 3-methyl-1-isopropylbutyl group, a 2-methyl- N-propoxy group, n-butoxy group, tert-butyl-2-methylpropyl group, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, methoxy group, ethoxy group, Butoxy group, n-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n- Group and _{-N (Q 1) (Q 2} ); And

A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; ;

Adjacent substituents of R ₂₀ to R ₂₈ are optionally bonded to each other to form a ring;

At least one of R ₂₀ to R ₂₈ is selected from the crosslinking groups represented by the above formulas 5-1 to 5-10;

Q ₁ and Q ₂ independently represent a hydrogen atom, a phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group; And

An ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group; A phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group substituted with at least one selected from the group consisting of a halogen atom, , But is not limited thereto.

As another example, in the general formula (6), R ₂₀ to R ₂₈ independently represent a crosslinking group, a hydrogen atom, a methyl group, an n-hexyl group, a phenyl group, a naphthyl group, A methoxy group and a group represented by the following general formulas (8-1) to (8-7);

Adjacent substituents of R ₂₀ to R ₂₈ are optionally bonded to each other to form a ring;

At least one of R ₂₀ to R ₂₈ may be selected from among the crosslinking groups represented by the above formulas (5-1) to (5-10), but is not limited thereto:

In the above formulas 8-1 to 8-7

* Is the binding site with neighboring atoms.

For example, in Formula 6, A 'represents a single bond, a C ₁ -C ₂₀ alkylene group, a C ₆ -C ₃₀ arylene group, and -N (Q ₄ ); And

A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; ;

Q ₄ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; And

C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; , But is not limited thereto.

As another example, in the above formula (6), A 'represents a single bond, a methylene group, a phenylene group and -N (Q ₄ ); And

A methylene group and a phenylene group substituted with at least one selected from a methyl group, an n-hexyl group and a phenyl group; ;

Q ₄ represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Isopropyl group, 1,2-dimethylbutyl group, n-heptyl group, n-hexyl group, n-hexyl group, Methylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl Methyl-1-isopropyl group, 1-tert-butyl-2-methyl-propyl group, phenyl group, naphthyl group, anthracenyl group and phenanthrenyl group; And

A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; , But is not limited thereto.

As another example, in the above formula (6), A 'represents a single bond, a methylene group, a phenylene group, and -N (Q ₄ ); And

A methylene group and a phenylene group substituted with at least one selected from a methyl group, an n-hexyl group and a phenyl group; ;

Q ₄ may be selected from a hydrogen atom, a methyl group, an n-hexyl group, a phenyl group, a naphthyl group and a group represented by the following formulas (8-1) to (8-6)

Among the above-mentioned formulas (8-1) to

* Is the binding site with neighboring atoms.

For example, in formula (6), (A ') _n5 represents a single bond, a C ₁ -C ₂₀ alkylene group, a C ₆ -C ₃₀ arylene group and a group represented by the following formula (2); And

A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; , But is not limited thereto: < Formula 2 >

In Formula 2,

L ₁ and L ₂ are, independently of each other, a single bond, a C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group; And

A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; ;

n3 and n4 are independently from each other selected from 1 and 2;

Ar ₁ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group, and a C ₆ -C ₃₀ aryl group; And

C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;

* Is the binding site with neighboring atoms.

For example, in Formula 6, at least one of R ₂₀ to R ₂₈ may be selected from crosslinking groups represented by the following Formulas 5-8 to 5-10, but is not limited thereto:

Of the above formulas 5-8 to 5-10,

* Is the binding site with neighboring atoms.

For example, the second repeating unit represented by the formula (6) may be represented by the following formula (6-1), but is not limited thereto:

(6-1)

In the above formula (6-1)

R ₁₇ to R ₂₈ , c, d, e, f, A ', n 5 and m 2 are as described in the above formula (6).

In another embodiment, the second repeating unit may be selected from the following structures, but is not limited thereto:

Among the above formulas,

n and m are, independently of each other, an integer of 1 to 10;

Since the second repeating unit is a triphenylamine-based unit having a crosslinking group, it can perform both a unit having a crosslinking group and a charge transporting unit. Therefore, the aminofluorene polymer containing the second repeating unit can increase the crosslinking property while increasing the proportion of the charge transporting unit as a whole (while securing a high charge transporting performance). Since the second repeating unit has a crosslinking group, a crosslinking reaction can take place by heating and / or irradiation of an active energy ray. By such a crosslinking reaction, a highly durable film which is not dissolved in a solvent can be formed. Therefore, the lifetime of the organic light emitting device using the aminofluorene polymer including the second repeating unit can be improved.

Further, for example, even when another layer is formed on the layer containing the aminofluorene polymer, the layer containing the aminofluorene polymer can not be dissolved or hardly dissolved in the solvent when the other layer is coated . It does not dissolve or hardly dissolve in the solvent at the time of coating.

When the aminofluorene polymer is a copolymer, the structure of the aminofluorene polymer is not particularly limited. For example, the aminofluorene polymer may be, but is not limited to, a random copolymer, an alternating copolymer, a periodic copolymer, and a block copolymer.

The ratio of the second repeating unit is preferably a ratio of the total number of repeating units forming the aminofluorene polymer (for example, when the aminofluorene polymer is composed of the first repeating unit and the second repeating unit, And the number of the second repeating units) of the first repeating unit is not less than 1 mol% and not more than 50 mol%. If the proportion of the second repeating unit is less than 1 mol%, a film insoluble in a solvent can not be formed by a cross-linking reaction, which may be undesirable. If the ratio of the second repeating unit is more than 50 mol%, the effect of improving the light emission lifetime of the organic light emitting device may be lowered, which may be undesirable.

For example, the proportion of the second repeating unit may be 5 mol% or more to 15 mol% or less and 10 mol% or less, but is not limited thereto, relative to the total repeating units forming the aminofluorene polymer.

In one embodiment, the sum of the content of the first repeating unit and the content of the second repeating unit may be 100 mol%. The aminofluorene polymer according to this embodiment may be a random copolymer represented by the following general formula (9), but is not limited thereto:

&Lt; Formula 9 >

In the formula (9)

R ₁ to R _4, F, F ', A, n 1, n 2 and m 1 refer to the description of Formula 1 above;

R ₁₇ to R ₂₈ , c, d, e, f, A ', n 5 and m 2 refer to the description of Formula 6 above;

q is an integer from 5 to 300;

r is an integer from 1 to 300;

The aminofluorene polymer represented by the above formula (9) may have sufficient resistance (insolubility) to a solvent during crosslinking. Therefore, even when another layer is formed on the layer containing the aminofluorene polymer, the layer containing the aminofluorene polymer is not dissolved or hardly dissolved in the solvent.

The proportion of each repeating unit can be arbitrarily adjusted by changing the ratio of the monomer used for polymerizing the aminofluorene polymer. The proportion of each repeating unit contained in the total repeating units can be measured by NMR.

The aminofluorene polymer may be formed by polymerizing a monomer represented by the following formula (1 '), but is not limited thereto:

&Lt; Formula (1) &gt;

In the above formula (1 '),

R ₁ to R ₄ , F, F ', A, n 1, n 2 and m 1, refer to the description in the above formula (1).

The monomer used for the aminofluorene polymer can be synthesized by a known synthesis method, and the structure of the monomer can be confirmed by using NMR and LC-MS.

The method of polymerizing the aminofluorene polymer is not particularly limited. For example, a known polymerization method such as a radical polymerization reaction, an anionic polymerization, or a cationic polymerization reaction can be used. As another example, it may be a radical polymerization reaction, but is not limited thereto.

Examples of the solvent used in the polymerization of the aminofluorene polymer include toluene, xylene, diethyl ether, chloroform, ethyl acetate, methylene chloride, tetrahydrofuran, acetone, acetonitrile, N, Sulfoxide, anisole, hexamethylphosphoric triamide, and the like. As another example, the solvent may be selected from toluene and tetrahydrofuran. The solvent may be used alone, or two or more solvents may be used together. The monomers used in the polymerization of aminofluorene polymers according to one embodiment of the present invention have a high solubility in the above solvents.

The monomer concentration in the solvent (or the total monomer when a plurality of monomers are used) may be 5 to 90% by weight with respect to the whole reaction solution. Specifically, the monomer concentration in the solvent may be 10 to 80% by weight, but is not limited thereto.

The polymerization temperature may be 40 to 150 DEG C from the viewpoint of molecular weight control, but is not limited thereto.

The polymerization reaction may be conducted for 30 minutes to 24 hours, but is not limited thereto.

The solvent to which the monomer is added may be degassed before addition of the polymerization initiator. For example, the degassing process may be freeze deaeration, degassing using an inert gas such as nitrogen gas, but is not limited thereto.

As the polymerization initiator, known ones can be used, for example, but not limited to, benzophenone, benzoyl peroxide, acetyl peroxide, lauroyl peroxide and azobisisobutyronitrile. The amount of the polymerization initiator to be added may be, for example, from 0.0001 to 1 mole based on 1 mole of all monomers used in the production of the aminofluorene polymer, but is not limited thereto.

The main chain terminal end of the above-mentioned aminofluorene polymer may be appropriately defined according to the type of material used, and may be, for example, a hydrogen atom, but is not limited thereto.

The method of synthesizing the aminofluorene polymer described above can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Organic light emitting device

Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described in detail with reference to FIG. 1 is a cross-sectional view of an organic light emitting diode 100 according to an embodiment of the present invention.

1 is a plan view of an organic light emitting device 100 according to an embodiment of the present invention in which an organic light emitting device 100 includes a substrate 110, a first electrode 120, a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, 170, and the second electrode 180, but the present invention is not limited thereto.

The organic light emitting device includes a single layer / light emitting layer / electron transport layer / second electrode having a first electrode / hole injecting function and a hole transporting function or a single layer / light emitting layer / electron transporting layer / Electron injecting layer / second electrode.

The aminofluorene polymer may be included in at least one organic layer disposed between the first electrode 120 and the second electrode 180. Specifically, the aminofluorene polymer may be included in the hole transport layer 140 from the viewpoint of longevity and high efficiency of the organic light emitting device.

The aminofluorene polymer may be more suitable for an organic light emitting device manufactured by a solution coating method.

The organic layer containing the aminofluorene polymer may be formed by a solution coating method. Specifically, the organic layer containing the aminofluorene polymer may be formed by spin coating, casting, micro gravure coat, gravure coat, bar coat, A roll coating method, a wire bar coat method, a dip coat method, a spry coat method, a screen printing method, a flexographic printing method, Method, an offset printing method, an ink jet printing method, or the like. In addition, any solvent may be used as long as it can dissolve the aminofluorene polymer in the solution coating method.

The method of forming the layer other than the organic layer including the aminofluorene polymer is not particularly limited. The layer other than the organic layer including the aminofluorene polymer may be deposited by, for example, vacuum evaporation or by solution coating.

The substrate 110 may be a substrate used as a typical organic light emitting device. For example, the substrate 110 may be a glass substrate, a semiconductor substrate, or a transparent plastic substrate.

The first electrode 120 is, for example, an anode. The first electrode 120 may be formed on the substrate 110 using a deposition method, a sputtering method, or the like. Specifically, the first electrode 120 may be formed of a metal, an alloy, a conductive compound or the like having a large work function. The first electrode 120 is, for example, transparent, conductive indium tin oxide is excellent _{(In 2 O 3 -SnO 2:} ITO), indium zinc oxide _{(In 2 O 3 -ZnO: IZO} ), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like. Also, the first electrode 120 may be formed as a reflective electrode using magnesium (Mg), aluminum (Al), or the like.

A hole injection layer 130 is formed on the first electrode 120. The hole injection layer 130 is a layer having a function of facilitating the injection of holes from the first electrode 120, specifically, about 10 nm to about 1000 nm, more specifically, about 10 nm to about 100 nm nm. &lt; / RTI &gt;

The hole injection layer 130 can be formed using a known material, for example, poly (ether ketone) -containing triphenylamine (TPAPEK), 4-isopropyl-4 ' -Methyldiphenyliodonium tetrakis (pentafluorophenyl) borate (PPBI), N, N'-diphenyl-N, N'-bis- [4 4,4'-diamine (DNTPD), copper phthalocyanine and the like, 4,4 ', 4 "-tris (3-methylphenylphenylamino) -phenyl] ), Triphenylamine (m-MTDATA), N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine Phenylamino} triphenylamine (TDATA), 4,4 ', 4 "-tris (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfona (poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (polyaniline / camphor sulfonic acid), PANI / PSS -styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)).

A hole transport layer 140 is formed on the hole injection layer 130. The hole transporting layer 140 is a layer containing a hole transporting material having a function of transporting holes, and may be about 10 nm to about 150 nm thick.

 The hole transporting layer 140 may be formed by solution coating using the aminofluorene polymer. According to the solution coating method, the aminofluorene polymer capable of improving the emission lifetime of the organic light emitting element 100 can be efficiently formed over a large area.

The hole transporting layer 140 can be formed using a known material in addition to the aminofluorene polymer described above. For example, the hole transporting layer 140 can be formed by using TAPC (1,1-bis [(di-4-tolylamino) phenyl] cyclohexane , Carbazole derivatives such as 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane, N-phenylcarbazole and polyvinylcarbazole, N- N'-diphenyl- [1,1-biphenyl] -4,4'-diamine, N, N'-bis (3-methylphenyl) -N, , 4'-diamine), TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine, 4,4' (naphthalen-2-yl) -N, N'-bis (phenyl) -benzidine, As shown in FIG.

A light emitting layer 150 is formed on the hole transport layer 140. The light emitting layer 150 is a layer that emits light such as phosphorescence or fluorescence light and may be formed on the hole transport layer 140 by using a vacuum deposition method, a spin coating method, an inkjet method, or the like. The light emitting layer 150 may be specifically about 10 nm to about 60 nm thick.

As the light emitting material of the light emitting layer 150, a known light emitting material can be used. However, the light emitting material contained in the light emitting layer 150 is preferably a light emitting material capable of emitting light (i.e., phosphorescence) from the triplet exciton. In this case, the light emitting lifetime of the organic light emitting diode 100 can be further improved.

Further, the light emitting layer 150 may include a different host material, e.g., 1,3-bis (carbazole) benzene (mCP), Alq ₃ (tris (8-quinolinolato) aluminum), CBP ( 4,4'-N, N'-dicabazole-biphenyl, 4,4'-N, N'-dicarbazole-biphenyl), poly (n-vinylcabazole) (Naphthalene-2-yl) anthracene, 9,10-di (naphthalene-2-yl) anthracene, TCTA, TPBI (1,3,5- ) benzene, 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene), TBADN (3-tert- butyl-9,10- Di (naphth-2-yl) anthracene), DSA (distyrylarylene, distyrylarylene), dmCBP (4.4'- bis (9- -Bis (9-carbazole) -2,2'-dimethylbiphenyl), 2,4,6-tris (diphenylamino) -1,3,5-triazine and the like.

The light emitting layer 150 may be formed as a light emitting layer that emits light of a specific color. For example, the light emitting layer 150 may be formed as a red light emitting layer, a green light emitting layer, and a blue light emitting layer.

When the light emitting layer 150 is a blue light emitting layer, known materials can be used as the blue dopant. For example, perylene and its derivatives, bis [2- (4,6-difluorophenyl) pyridinate ] Iridium (Ir) complexes such as picolinate iridium (III) (FIrpic) and the like can be used.

When the light emitting layer 150 is a red light emitting layer, known materials can be used as the red dopant. For example, rubrene and its derivatives, DCM (4- (Dicyanomethylene) -2-methyl-6- [ pyran) and its derivatives, Ir (piq) ₂ (p-dimethylamino) styryl] -4H-pyran, 4- (dicyanomethylene) an iridium complex such as acac (bis (1-phenylisoquinoline) (acetylacetonate) iridium (III)), an osmium (Os) complex or a platinum complex.

For example, coumarin and its derivatives, tris (2-phenylpyridine) iridium (III) (Ir (ppy) ₃ ) Iridium complexes such as tris (2- (3-p-xylyl) phenyl) pyridine iridium (III) (TEG) and tris (acetylacetonato) iridium (III) (Ir (acac) ₃ ) .

An electron transport layer 160 is formed on the light emitting layer 150. The electron transporting layer 160 is a layer containing an electron transporting material having a function of transporting electrons and may be formed on the light emitting layer 150 by using a vacuum deposition method, a spin coating method, an inkjet method, or the like. The electron transporting layer 160 may be formed to a thickness of, for example, about 15 nm to about 50 nm.

The electron transporting layer 160 can be formed using a known electron transporting material. Examples thereof include tris (8-quinolinato) aluminum ( _Alq3 ) and nitrogen - a compound having an aromatic ring and the like. Specific examples of the compound having a nitrogen-containing aromatic ring include 1,3,5-tri [(3-pyridyl) -phen-3-yl] benzene (1,3,5-tri [ (pyridine-3-yl) biphenyl-3-yl) -1,3 , Triazine ring such as 5-triazine (2,4'-triazine (3 '- (pyridin-3-yl) biphenyl-3-yl) -1,3,5- - (4- (N-phenylbenzoimidazol-1-yl-phenyl) -9,10-dinaphthylanthracene (2- (4- (N-phenylbenzoimidazolyl- dinaphthylthracene, etc. These electron transport layer forming materials may be either commercially available products or synthetic ones. Examples of commercially available products include KLET-01, KLET-02 , KLET-03, KLET-10, KLET-M1 (available from Chemipro Kasei), etc. These electron transport layer forming materials may be used alone Two or more species may be mixed and used.

An electron injection layer 170 is formed on the electron transport layer 160. The electron injection layer 170 is a layer having a function of facilitating injection of electrons from the second electrode 180, and may be formed on the electron transport layer 160 using a vacuum deposition method or the like. The electron injection layer 170 may be formed to a thickness of about 0.3 nm to about 9 nm.

The electron injecting layer 170 can be formed using a known electron injecting material. For example, the (8-quinolinato) lithium (Liq), lithium fluoride (LiF) For example, by using sodium (NaCl), cesium fluoride (CsF), lithium oxide (Li ₂ O), barium oxide (BaO) or the like.

A second electrode 180 is formed on the electron injection layer 170. The second electrode 180 may be, for example, a cathode. Specifically, the second electrode 180 may be formed of a metal, an alloy, a conductive compound or the like with a small work function. The second electrode 180 may be formed of a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca) or the like or an aluminum- ), Magnesium-silver (Mg-Ag), or the like. In addition, the second electrode 180 can be formed as a transmissive electrode using indium tin oxide (ITO), indium zinc oxide (IZO) or the like of 20 nm or less.

The organic light emitting diode 100 may be a front emission type or a back emission type.

Although the structure of the organic light emitting device 100 according to the embodiment of the present invention has been described above, the structure of the organic light emitting device 100 according to one embodiment of the present invention is not limited to the above example .

The organic light emitting device 100 according to an embodiment of the present invention may be formed using various structures of known organic light emitting devices. For example, the organic light emitting device 100 may not have one or more layers of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170. Each layer of the organic light emitting diode 100 may be formed as a single layer or a plurality of layers.

The organic light emitting diode 100 may include a hole blocking layer between the hole transport layer 140 and the light emitting layer 150 to prevent triplet excitons or holes from diffusing into the electron transport layer 160. The hole blocking layer can be formed, for example, by an oxadiazole derivative, a triazole derivative, a phenanthroline derivative or the like.

In the present specification, the C ₁ -C ₂₀ alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 20 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl A tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. In the present specification, a C ₁ -C ₂₀ alkylene group means a divalent group having the same structure as the C ₁ -C ₁₀ alkyl group.

The C ₁ -C ₂₀ alkoxy group in the present specification means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₂₀ alkyl group), and specific examples thereof include methoxy group, ethoxy group , Isopropyloxy group, and the like.

In the present specification, the C ₁ -C ₂₀ oxyalkylene group means that some of the carbon atoms constituting the C ₁ -C ₂₀ alkylene group are replaced by oxygen.

In the present specification, the C ₃ -C ₁₆ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 16 carbon atoms participating in the ring formation, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group , A cyclohexyl group, a cycloheptyl group, and the like. In the present specification, the C ₃ -C ₁₆ cycloalkylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

The C ₃ -C ₁₆ cycloalkoxy group in the present specification means a monovalent group having a formula of -OA ₁₀₂ (wherein A ₁₀₂ is the above C ₃ -C ₁₆ cycloalkyl group), and specific examples thereof include cyclopropone A cyclobutoxy group, a cyclopentoxy group, and the like.

The term C ₃ -C ₁₆ oxycycloalkylene group in the present specification means that some of the carbon atoms constituting the C ₃ -C ₁₆ cycloalkylene group are replaced by oxygen.

The C ₆ -C ₃₀ aryl groups of the specification, means a number of carbon atoms is 1 the (monovalent) having an aromatic system when one of 6 to 30 carbonyl groups involved in ring formation, and, C ₆ -C ₃₀ arylene group having 6 to Quot; means a divalent group having 30 carbocyclic aromatic systems. Specific examples of the C ₆ -C ₃₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group and the like. The C ₆ -C ₃₀ aryl groups and C ₆ -C ₃₀ aryl If the alkylene group contains two or more rings, the 2 or more rings may be fused to each other.

The specification of the C ₆ -C ₃₀ aryloxy group -OA ₁₀₃ refers to (wherein, A ₁₀₃ is the C ₆ -C ₃₀ aryl group).

The C ₆ -C ₃₀ aryloxy arylene group of the specification, means that some of the carbon constituting the C ₆ -C ₃₀ arylene group is replaced by oxygen.

The C ₅ -C ₃₀ heteroaryl group in the present specification includes at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, and includes 5 to 30 heterocyclic Aromatic group, wherein the C ₅ -C ₃₀ heteroarylene group comprises at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, Means a divalent group having from 5 to 30 carbon atoms in the heterocyclic aromatic system. Specific examples of the C ₅ -C ₃₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₅ -C ₃₀ heteroaryl group and the C ₅ -C ₃₀ heteroarylene group include two or more rings, two or more rings may be condensed with each other.

In the present specification, the C ₇ -C ₄₀ aralkyl group means a monovalent group in which the alkyl group and the aryl group constituting the C ₇ -C ₄₀ aralkyl group have 7 to 40 carbon atoms. Specific examples of the C ₇ -C ₄₀ aralkyl group include a benzyl group, a phenylethyl group, a methylbenzyl group, a naphthylmethyl group, and the like.

In the present specification, the "halogen atom" may be selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Hereinafter, the compound and organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples. In the following Synthesis Examples, the molar equivalent of A and the molar equivalent of B in the expression "B was used instead of A"

Hereinafter, the aminofluorene polymer and the organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples.

[Example]

Analysis was performed according to the method described below in the following Synthesis Examples.

(1) Measurement of number average molecular weight, weight average molecular weight and dispersion degree

The number average molecular weight (Mn), the weight average molecular weight (Mw) and the degree of dispersion (Mw / Mn) were measured by GPC (gel permeation chromatography) using polystyrene as a standard sample under the following conditions.

Analytical equipment: product of Shimadzu Corporation, product name: Prominence

Column: PLgel MIXED-B manufactured by Polymer Labs

Column temperature: 40 ° C

Flow rate: 1.0 mL / min

Injection volume: 20 μL

Solvent: tetrahydrofuran (THF) (concentration: about 0.05% by weight)

Detector: UV-VIS detector (product name: SPD-10AV manufactured by Shimadzu Corporation)

Standard sample: Polystyrene

Synthesis Example 1: Synthesis of Compound 100

1) Synthesis of monomer A

The monomer A was synthesized as shown in the following reaction formula.

2,7-dibromo-9,9-dioctylfluorene (50.00 g, 91.17 mmol) was placed in a 2 L three-necked flask and purged with argon ). Tetrahydrofuran (750 ml) was added to the flask, cooled to -75 캜 in an acetone / dry ice bath, and stirred for 15 minutes. 1.6 M n-butyl lithium (n-BuLi) (36.12 ml, 95.72 mmol, hexane solution) was added dropwise to the flask and stirred for 1 hour. To the flask was added triisopropyl borate (20.58 ml, 109.40 mmol) and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, extraction was performed using ethyl acetate, and the extracted organic layer was concentrated. The organic layer was concentrated, and the obtained solid was recrystallized using chloroform and hexane to obtain Compound 1. [

Next, a 500 ml three-necked flask was charged with Compound 1 (15.00 g, 29.22 mmol), iodobenzene (6.56 g, 32.14 mmol), tetrakis (triphenylphosphine) palladium 0) (1.01 g, 0.88 mmol) and sodium carbonate (24.77 g, 233.75 mmol) were charged, and argon was charged. Ethanol (15 ml), water (100 ml) and toluene (116 ml) were added to the flask, and the mixture was stirred at 85 ° C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite (registered trademark). After water was added to the filtrate, the mixture was extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give compound 2. &lt; 1 &gt;

(15.00 g, 27.49 mmol), pinacol diborane (7.68 g, 30.24 mmol), 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) Pd (dppf) Cl ₂ .CH ₂ Cl ₂ ) (0.34 g, 0.41 mmol) and potassium acetate (potassium iodide) were added to a solution of potassium iodide in tetrahydrofuran acetate) (8.09 g, 82.47 mmol) was charged, and argon was charged. Anhydrous 1,4-dioxane (110 ml) was added to the flask, and the mixture was stirred at 100 ° C for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Activated carbon (10 g) was added to the filtrate, and the mixture was stirred at 100 ° C for 1 hour. Then, activated carbon was removed by using Celite, and the filtrate was concentrated. The filtrate was concentrated, and the resulting solid was washed with acetonitrile (25 ml) at room temperature to give compound 3.

 Compound 3 (3.90 g, 6.59 mmol), N, N-bis (4-bromophenyl) -N, N-bis (4-methylphenyl) -9,9-dioctyl-9H- N-bis (4-methylphenyl) -9,9-dioctyl-9H-fluorene-2,7-diamine (6.00 g, And bis (triphenylphosphine) palladium (II) dichloride (0.23 g, 0.33 mmol) were charged and charged with argon. Tetraethyl ammonium hydroxide (3.88 g, 26.35 mmol) and anhydrous toluene (300 ml) were added to the flask, and the mixture was stirred at 100 ° C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Water was added to the filtrate, extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give a light green solid. The resulting solid was recrystallized from tetrahydrofuran and methanol to obtain Compound (4).

Compound 4 (4.00 g, 3.08 mmol), 9,9-dioctyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (9,9-dioctyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluorene- 2-carboxaldehyde (1.65 g, 3.02 mmol), palladium (II) acetate (0.035 g, 0.15 mmol), tris (2-methoxyphenyl) phosphine ) (0.22 g, 0.62 mmol) were charged, and argon was charged. Tetraethylammonium hydroxide (1.82 g, 2.40 mmol) and anhydrous toluene (10 ml) were added to the flask, and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Water was added to the filtrate, extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give compound 5.

Compound 5 (3.80 g, 2.32 mmol) and methyltriphenylphosphonium iodide (1.31 g, 3.26 mmol) were placed in a 50 ml three-necked flask and filled with argon. To the flask was added tetrahydrofuran (26 ml), cooled to 0 C in an ice bath, potassium tert-butoxide (0.34 g, 3.01 mmol) was added and the mixture was stirred. After completion of the reaction, water was added, extraction was performed using toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give a light yellow solid. The obtained solid was dissolved in tetrahydrofuran and then re-precipitated with methanol to obtain monomer A.

The obtained monomer A was identified by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.77-7.36 (m, 23H), 7.10-6.90 (m, 16H), 6.81 (dd, J = 17.4 Hz, 10.8 Hz, 1H), 5.80 (d, J = 17.4 Hz, 1H), 5.26 (d, J = 11.4 Hz, 1H), 2.35 (s, 6H), 2.06-1.96 (m, 8H), 1.83-1.77 (m, 2H), 1.53-1.06 (m , 60H), 0.88-0.71 (m, 30H)

2) Synthesis of monomer B

Monomer B was synthesized by the following reaction formula.

(10.00 g, 19.03 mmol), pinacol diborane (5.80 g, 22.83 mmol), Pd (dppf) Cl ₂ .CH ₂ Cl ₂ (0.56 g, 0.68 mmol) and potassium acetate 5.60 g, 57.09 mmol) were charged, and argon was charged. Anhydrous 1,4-dioxane (100 ml) was added to the flask, and the mixture was stirred at 100 ° C for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Activated carbon (10 g) was added to the filtrate, and the mixture was stirred at 100 ° C for 1 hour. Then, activated carbon was removed by using Celite, and the filtrate was concentrated. The filtrate was concentrated, and the resulting solid was washed with acetonitrile (25 ml) at room temperature to give compound 7.

 Compound (7) (0.95 g, 1.66 mmol), N, N-bis (4-bromophenyl) -N, N-bis (4-methylphenyl) -9,9-dioctyl-9H- Diamine (1.51 g, 1.66 mmol) and bis (triphenylphosphine) palladium (II) dichloride (0.06 g, 0.09 mmol) were charged and argon was charged. Tetraethylammonium hydroxide (2.44 g, 16.59 mmol) and anhydrous toluene (47 ml) were added to the flask, and the mixture was stirred at 100 ° C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Water was added to the filtrate, extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give a light green solid. The resulting solid was recrystallized from tetrahydrofuran and methanol to obtain Compound 8.

In a 50 ml three-necked flask, Compound 8 (1.00 g, 0.60 mmol), 9,9-dioctyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- (0.33 g, 0.60 mmol), palladium (II) acetate (0.007 g, 0.03 mmol), tris (2-methoxyphenyl) phosphine (0.04 g, 0.20 mmol ), And argon was charged. Tetraethylammonium hydroxide (0.35 g, 2.40 mmol) and anhydrous toluene (10 ml) were added to the flask, and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Water was added to the filtrate, extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to obtain Compound 9.

 Compound 9 (0.73 g, 0.45 mmol) and methyltriphenylphosphonium iodide (0.25 g, 0.63 mmol) were placed in a 100 ml three-necked flask, and argon was charged. To the flask was added tetrahydrofuran (50 ml), cooled to 0 C in an ice bath, and potassium tert-butoxide (0.06 g, 0.59 mmol) was added to stir the mixture. After completion of the reaction, water was added, extraction was performed using toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to give a light yellow solid. The resulting solid was dissolved in tetrahydrofuran and then re-precipitated with methanol to obtain monomer B.

The obtained monomer B was confirmed by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.81-6.90 (m, 46H), 6.81 (dd, J = 17.4 Hz, 10.8 Hz, 1H), 5.80 (d, J = 17.4 Hz, 1H), 5.26 (d, J = 11.4 Hz, 1H), 3.09 (s, 8H), 2.35 (s, 6H), 2.01-1.96 (m, 4H), 1.80-1.75 ), 0.87-0.69 (m, 12H)

3) Synthesis of Compound 100

Using the monomers A and B synthesized above, a compound 100 having the structure shown below was synthesized.

<Compound 100>

Monomer A (1000 mg) Monomer B (105.0 mg), azobisisobutyronitrile (2.0 mg) and toluene (2.8 ml) were placed in a Schlenk flask and bubbled. Degassed, and the mixture was heated and stirred at 80 DEG C for 6.5 hours. The reaction mixture was cooled to room temperature, reprecipitated seven times with tetrahydrofuran as a good solvent and methanol / acetone as a bad solvent, and the resulting precipitate was vacuum-dried.

0.85 g of Compound 100 which is a random copolymer of Monomer A and Monomer B (provided that the ratio of the constituent unit Aa derived from monomer A to the constituent unit Bb derived from monomer B is Aa: Bb = 90: 10). Compound 100 had a number average molecular weight (Mn) of 35,800, a weight average molecular weight (Mw) of 74,600 and a degree of dispersion (Mw / Mn) of 2.08.

Synthesis Example 2: Synthesis of Compound 101

1) Synthesis of monomer C

Monomer C was synthesized by the following reaction formula.

Compound 10 was synthesized using the same method as the synthesis of Compound 9, except that Compound 7 was used instead of Compound 8. Monomer C was synthesized using the same method as for the synthesis of Monomer B except that Compound 10 was used instead of Compound 9.

The obtained monomer C was confirmed by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.84 (d, J = 7.8, 2H), 7.71-7.50 (m, 10H), 7.44-7.20 (m, 9H), 6.70-6.93 (m, 2H) , 6.81 (dd, J = 17.4 Hz, 10.8 Hz, 1H), 5.80 (d, J = 18.0 Hz, 1H), 5.24 (d, J = 11.4 Hz, 1H), 3.09 (s, 8H), 2.00-1.95 (m, 4H), 1.21-1.05 (m, 20H), 0.82-0.66 (m, 10H)

2) Synthesis of Compound 101

Compound 101, which is a random copolymer of Monomer A and Monomer C having the structure shown below, was synthesized in the same manner as in the synthesis of Compound 100, except that Monomer C was used instead of Monomer B. The ratio of the constituent unit Aa derived from monomer A to the constituent unit Cc derived from monomer C was Aa: Cc = 90: 10. The compound 101 had a number average molecular weight (Mn) of 58,100, a weight average molecular weight (Mw) of 155,500 and a degree of dispersion (Mw / Mn) of 2.67.

&Lt; Compound 101 >

Synthesis Example 3: Synthesis of Compound 102

1) Synthesis of monomer D

The monomer D was synthesized by the following reaction formula.

Compound 12 was synthesized in the same manner as in the synthesis of Compound 8, except that Compound 11 was used instead of Compound 7. Compound 13 was synthesized in the same manner as in the synthesis of Compound 9, except that Compound 12 was used instead of Compound 8. The monomer D was synthesized in the same manner as the synthesis of the monomer B except that the compound 13 was used instead of the compound 9.

The obtained monomer D was confirmed by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.74-7.63 (m, 4H), 7.56-7.48 (m, 10H), 7.41-7.28 (m, 5H), 7.19-7.09 (m, 16H), 6.81 (dd, J = 17.4Hz, 10.8Hz , 1H), 5.80 (d, J = 17.4 Hz, 1H), 5.26 (d, J = 11.4 Hz, 1H), 2.35 (s, 6H), 2.01-1.96 (m , 8H), 1.82-1.77 (m, 4H), 1.30-1.13 (m, 60H), 0.88-0.67 (m, 30H)

2) Synthesis of monomer E

Compound 15 was synthesized in the same manner as in the synthesis of Compound 7, except that Compound 14 was used instead of Compound 6. Compound 16 was synthesized in the same manner as in the synthesis of Compound 9, except that Compound 15 was used instead of Compound 8. The monomer E was synthesized using the same method as the synthesis of the monomer B except that the compound 16 was used instead of the compound 9.

The obtained monomer E was identified by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.83-7.63 (m, 2H), 7.54-7.50 (m, 4H), 7.43-7.23 (m, 7H), 7.18-7.16 (m, 2H), 6.95 -6.91 (m, 4H), 6.81 (dd, J = 17.4 Hz, 10.8 Hz, 1H), 5.80 (d, J = 18.0 Hz, 1H), 5.24 (d, J = 11.4 Hz, 1H), 3.09 (s , 8H), 2.00-1.94 (m, 7H), 1.21-1.04 (m, 20H), 0.81-0.64 (m, 10H)

3) Synthesis of Compound 102

Compound 102, which is a random copolymer of monomers D and E, was synthesized in the same manner as the synthesis of Compound 100, except that monomers D and E were used instead of monomers A and B. The ratio of the constituent unit Dd derived from the monomer D to the constituent unit Ee derived from the monomer E was Dd: Ee = 90: 10. Compound 102 had a number average molecular weight (Mn) of 74,000, a weight average molecular weight (Mw) of 195,000 and a degree of dispersion (Mw / Mn) of 2.60.

&Lt; Compound 102 >

Synthesis Example 4: Synthesis of Compound 103

1) Synthesis of monomer F

Monomer F was synthesized by the following reaction formula.

(1.66 g, 2.79 mmol), ditolylamine (0.50 g, 2.53 mmol), copper iodide (CuI) (0.02 g, 0.13 mmol), trans-1, Cyclohexanediamine (0.06 g, 0.51 mmol) and sodium tert-butoxide (0.54 g, 5.58 mmol) were charged and argon was charged. To the flask was added anhydrous 1,4-dioxane (5 ml) and the mixture was stirred at 100 &lt; 0 &gt; C for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. The filtrate was concentrated, and the concentrate was purified by column chromatography to obtain Compound 18.

(1.00 g, 1.50 mmol), p-toluidine (0.21 g, 1.96 mmol), tris (dibenzylideneacetone) dipalladium (0) (tris (dibenzylideneacetone) dipalladium (0): Pd ₂ (dpa) ₃ ) (0.07 g, 0.08 mmol), 1,1'-bis (diphenylphosphino) ferrocene: dppf (0.13 g, 0.23 mmol) and sodium tert-butoxide (0.29 g, 3.01 mmol) were charged, and argon was charged. To the flask was added toluene (2 ml) and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. Water was added to the filtrate, extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to obtain Compound 19.

 (1.00 g, 14.50 mmol), 1-bromo-4-iodobenzene (4.50 g, 15.92 mmol), copper iodide (I) (0.15 g , Trans-1,2-cyclohexanediamine (0.33 g, 2.89 mmol) and sodium tert-butoxide (2.78 g, 28.04 mmol) were charged and argon was charged. To the flask was added anhydrous 1,4-dioxane (14 ml) and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and impurities were separated by filtration using Celite. The filtrate was concentrated, and the concentrate was purified by column chromatography to obtain Compound 20.

Compound 21 was synthesized in the same manner as in the synthesis of Compound 9, except that Compound 20 was used instead of Compound 8. Monomer F was synthesized in the same manner as in the synthesis of Monomer B except that Compound 21 was used instead of Compound 9.

The obtained monomer F was confirmed by H ¹ -NMR.

^{1 H-NMR (300 MHz,} CDCl 3): σ 7.71-7.37 (m, 10H), 7.28-7.04 (m, 18H), 6.81 (dd, J = 17.4 Hz, 10.8 Hz, 1H), 5.80 (d, J = 18.0 Hz, 1H), 5.24 (d, J = 11.4 Hz, 1H), 2.35 (s, 9H), 2.01-1.96 (m, 4H), 1.79-1.73 (m, 4H), 1.29-1.05 (m , 40H), 0.88-0.68 (m, 20H)

2) Synthesis of Compound 103

The following compound 103 was synthesized using the same method as the synthesis of the compound 100 except that the monomers E and F were used instead of the monomers A and B. The ratio of the constituent unit Ee derived from the monomer E to the constituent unit Ff derived from the monomer F was Ee: Ff = 90: 10. Compound 103 had a number average molecular weight (Mn) of 38,000, a weight average molecular weight (Mw) of 93,000 and a dispersion degree (Mw / Mn) of 2.4.

<Compound 103>

Example 1

The organic light emitting device shown in Fig. 1 was produced by the following method.

The ITO glass substrate on which the stripe-shaped ITO (thickness: 150 nm) (anode) was disposed was spin-coated with PEDOT / PSS (Sigma-Aldrich product) so as to have a thickness of 30 nm to form a hole injection layer.

Next, Compound 100 (1 wt%, xylene solution) was spin-coated on the hole injection layer in a nitrogen atmosphere, and then heat-treated on a hot plate at 230 캜 for 1 hour to form a hole transporting layer having a thickness of 30 nm.

Then, a mixture of 1,3-bis ( N -carbazolyl) benzene (hereinafter referred to as mCP) and 4,4'-bis (carbazol-9- (III) (hereinafter referred to as TEG) dopant was co-evaporated in a vacuum evaporator to form a 30 nm thick light emitting layer (total mass of the light emitting layer , The dopant was 10 mass%). TEG is a luminescent material capable of emitting light (phosphorescence) in triplet excitons.

Subsequently, the substrate formed up to the light emitting layer was introduced into a vacuum evaporator, and Liq and KLET-03 were co-deposited to form an electron transporting layer having a thickness of 50 nm on the light emitting layer.

Subsequently, an electron injecting material (LiF) was deposited to a thickness of 1 nm.

Subsequently, aluminum was deposited on the electron injection layer to form a cathode (cathode) having a thickness of 100 nm to prepare an organic light emitting device.

Example 2

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 101 was used instead of Compound 100.

Example 3

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 102 was used instead of Compound 100.

Example 4

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 103 was used instead of Compound 100.

Comparative Example 1

An organic light emitting device was prepared in the same manner as in Example 1 except that the following compound c1 was used instead of the compound 100: The following compound c1 is a random copolymer containing no repeating unit having a fluorene structure, and n and m are molar ratios of 90:10. The following compound c1 has a number average molecular weight (Mn) of 24,000 and a weight average molecular weight (Mw) of 64,000.

<Compound c1>

Evaluation example

The current efficiency and the luminescence lifetime of the organic luminescent devices of Examples 1 to 4 and Comparative Example 1 were evaluated by the following methods. The results are shown in Table 1 below. The current efficiency and the luminescent lifetime in the following Table 1 are expressed as a relative value to the current efficiency and the luminescent lifetime in the following Comparative Example 1 and show relative values when the current efficiency and the luminescent lifetime in Comparative Example 1 are taken as 100, respectively.

(1) Current efficiency

A predetermined voltage was applied to the organic light emitting device using a DC constant voltage power source (for example, a source meter manufactured by KEYENCE) to emit the organic light emitting device. The current to be applied to the organic light emitting element is gradually increased while measuring the light emission of the organic light emitting element using a luminance measuring apparatus (for example, SR-3: Topcom). The current was kept constant when the luminance reached 1000 cd / m ² . The current efficiency (cd / A) was calculated by calculating the current value (current density) per unit area of the organic light emitting device and calculating the luminance cd / m ² from the current density A / m ₂ . The current efficiency indicates the efficiency of converting current into light emitting energy, which means that the performance of the organic light emitting device is higher.

(2) Luminescent lifetime

The time taken until the luminance value measured by the luminance measuring apparatus decreased to become 80% of the initial luminance was defined as "luminous lifetime ".

Hole transport layer Current efficiency Luminescent lifetime Example 1 Compound 100 120 1630 Example 2 Compound 101 112 540 Example 3 Compound 102 118 2000 Example 4 Compound 103 110 910 Comparative Example 1 Compound c1 100 100

Referring to the results of Table 1, it can be seen that the current efficiency and the luminescence lifetime of Examples 1 to 4 are improved as compared with Comparative Example 1. [

The aminofluorene polymer not only enables efficient film formation by the solution coating method, but also can improve the lifetime of the organic light emitting device.

100: organic light emitting device,
110: substrate
120: first electrode
130: Hole injection layer
140: hole transport layer
150: light emitting layer
160: electron transport layer
170: electron injection layer
180: second electrode

Claims (20)

1. An aminofluorene polymer comprising a first repeating unit represented by the following formula (1): < EMI ID =
&Lt; Formula 1 &gt;

In Formula 1,
R ₁ to R ₃ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group; ;
m1 is an integer from 1 to 20;
F and F 'are independently selected from a substituted or unsubstituted azafluorenylene group and a substituted or unsubstituted fluorenylene group;
n1 and n2 are independently selected from 1 and 2;
A is a group represented by the following formula (2);
R ₄ represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and _{-N (Q 1) (Q 2} ) ;
(2)

In Formula 2,
L ₁ and L ₂ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ A substituted or unsubstituted C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ oxycycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ oxyarylene group, a substituted or unsubstituted aryl group, a C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene _{group, -Si (Q 4) (Q} 5) - and -N (Q ₄₎ - is selected from;
n3 and n4 are independently from each other selected from 1 and 2;
Ar ₁ represents a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, An unsubstituted C ₅ -C ₃₀ heteroaryl group and -N (Q ₆ ) (Q ₇ );
Ar ₁ is optionally fused with F, F ', L ₁ or L ₂ to form a ring;
Q ₁ to Q ₇ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;
* Is the binding site with neighboring atoms. The method according to claim 1,
R ₁ to R ₃ are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an n-propyl group and an n-butyl group. The method according to claim 1,
F and F 'independently of one another are a group represented by the following general formula (3): Aminofluorene polymer:
(3)

In Formula 3,
R ₅ to R ₈ independently represent a bond site, a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group , substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ - C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and -N (Q ₁ ) (Q ₂ );
Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;
Two of R ₅ to R ₈ are a bonding site;
Q ₁ to Q ₃ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;
a and b are independently selected from 1, 2, 3 and 4;
Y ₁ to Y ₈ are, independently of each other, a carbon atom or a nitrogen atom. The method of claim 3,
R ₅ to R ₈ independently represent a bond site, a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, Isopropyl group, 1,2-dimethylpropyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, Ethylbutyl, n-butyl, isobutyl, n-butyl, isobutyl, Methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5- N-hexadecyl group, n-pentadecyl group, n-hexadecyl group, n-hexadecyl group, N-heptadecyl group, n-octadecyl group, n-nonadecyl group and n-eicosyl group, phenyl group, naphthyl group, A phenanthrenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group and a thiophenyl group;
-F, a methyl group, an ethyl group and an n-propyl group substituted with at least one selected from a phenyl group and a naphthyl group; And
A phenyl group substituted with a methyl group and a tert-butyl group substituted with a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- A phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group and a thiophenyl group which are substituted with at least one selected from a phenyl group substituted with a butyl group; ;
Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;
And the two substituents R ₅ to R ₈ are binding sites. The method according to claim 1,
F and F 'independently of one another are selected from the groups represented by the following formulas (4-1) to (4-58): Aminofluorene polymer:

Of the above-mentioned formulas (4-1) to (4-58)
Two hydrogen atoms are replaced by binding sites. The method according to claim 1,
R ₄ is a hydrogen atom, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₃₀ aryl group, a C ₁ -C ₂₀ alkoxy group and -N (Q ₁ ) (Q ₂ ); And
C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;
Q ₁ and Q ₂ are, independently of each other, a hydrogen atom, a C ₆ -C ₃₀ aryl group; And
A C ₆ -C ₃₀ aryl group substituted with at least one selected from C ₁ -C ₂₀ alkyl groups; &Lt; / RTI &gt; aminofluorene polymer. The method according to claim 1,
R ₄ represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Isopropyl group, 1,2-dimethylbutyl group, n-heptyl group, n-hexyl group, n-hexyl group, Methylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl Methyl-1-propyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a methoxy group, an ethoxy group, n-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group and -N (Q ₁ ) (Q _2); And
A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; ;
Q ₁ and Q ₂ independently represent a hydrogen atom, a phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group; And
An ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group; A phenyl group, a naphthyl group, an anthracenyl group and a phenanthrenyl group substituted with at least one selected from the group consisting of a halogen atom, &Lt; / RTI &gt; aminofluorene polymer. The method according to claim 1,
L ₁ and L ₂ are, independently of each other, a single bond, a C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group; And
A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; &Lt; / RTI &gt; aminofluorene polymer. The method according to claim 1,
L ₁ and L ₂ are, independently of each other, a single bond, a methylene group and a phenylene group; And
A methylene group and a phenylene group substituted with at least one selected from a methyl group, an n-hexyl group and a phenyl group; &Lt; / RTI &gt; aminofluorene polymer. The method according to claim 1,
Ar ₁ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group, and a C ₆ -C ₃₀ aryl group; And
C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;
Ar ₁ is optionally fused to F, F ', L ₁ or L ₂ to form a ring. The method according to claim 1,
Ar ₁ represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Isopropyl group, 1,2-dimethylbutyl group, n-heptyl group, n-hexyl group, n-hexyl group, Methylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl Methyl-1-isopropyl group, 1-tert-butyl-2-methyl-propyl group, phenyl group, naphthyl group, anthracenyl group and phenanthrenyl group; And
A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethyl Propyl group, n-propyl group, isopropyl group, n-propyl group, isopropyl group, n-butyl group, A phenyl group substituted with at least one member selected from the group consisting of an isopropoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, Anthracenyl group, and phenanthrenyl group; ;
Ar ₁ is optionally fused to F, F ', L ₁ or L ₂ to form a ring. The method according to claim 1,
The first repeating unit represented by the general formula (1) is an aminofluorene polymer represented by the general formula (1-1)
<Formula 1-1 '

In Formula 1-1,
R ₁ to R ₃ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group; ;
m1 is an integer from 1 to 20;
F and F 'are independently selected from a substituted or unsubstituted azafluorenylene group and a substituted or unsubstituted fluorenylene group;
n1 and n2 are independently selected from 1 and 2;
A is a group represented by the following formula (2);
R ₄ represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and _{-N (Q 1) (Q 2} ) ;
(2)

In Formula 2,
L ₁ and L ₂ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ A substituted or unsubstituted C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ oxycycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ oxyarylene group, a substituted or unsubstituted aryl group, a C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene _{group, -Si (Q 4) (Q} 5) - and -N (Q ₄₎ - is selected from;
n3 and n4 are independently from each other selected from 1 and 2;
Ar ₁ represents a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, An unsubstituted C ₅ -C ₃₀ heteroaryl group and -N (Q ₆ ) (Q ₇ );
Ar ₁ is optionally fused with F, F ', L ₁ or L ₂ to form a ring;
* Is the binding site with neighboring atoms;
R ₅ to R ₈ independently represent a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted Or an unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkoxy group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl _{group, -Si (Q 1) (Q} 2) (Q 3) , and -N (Q is selected from ₁₎ (Q _2);
Adjacent substituents of R ₅ to R ₈ are optionally bonded to each other to form a ring;
a and b are independently selected from 1, 2, 3 and 4;
Y ₁ to Y ₈ are, independently of each other, a carbon atom or a nitrogen atom;
Q ₁ to Q ₇ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group. The method according to claim 1,
Wherein the first repeating unit represented by Formula 1 is selected from the group consisting of aminofluorene polymers:

In the above formulas, m is an integer of 1 to 10. The method according to claim 1,
Further comprising a second repeating unit derived from a monomer containing at least one selected from crosslinking groups represented by the following general formulas (5-1) to (5-10):

Of the above formulas (5-1) to (5-10)
R ₁₀ to R ₁₆ are, independently from each other, a hydrogen atom or a substituted or unsubstituted C ₁ -C ₂₀ alkyl group;
p is an integer from 1 to 10;
* Is the binding site with neighboring atoms. 15. The method of claim 14,
Wherein the second repeating unit is represented by the following formula (6): < EMI ID =
(6)

In Formula 6,
R ₁₇ to R ₁₉ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, or a substituted or unsubstituted C ₆ -C ₃₀ aryl group,
R ₂₀ to R ₂₈ independently represent a crosslinking group, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group , A substituted or unsubstituted C ₃ -C ₁₆ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₆ A substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, a substituted or unsubstituted C ₇ -C ₄₀ aralkyl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, -Si (Q ₁ ) is selected from (Q ₂₎ (Q _3), and _{-N (Q 1) (Q 2} );
Adjacent substituents of R ₂₀ to R ₂₈ are optionally bonded to each other to form a ring;
At least one of R ₂₀ to R ₂₈ is selected from the crosslinking groups represented by the following formulas (5-1) to (5-10);
c, d, e and f are independently of each other selected from 1, 2 and 3;
A 'is a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₆ cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a C ₁ -C ₂₀ oxyalkylene group, a substituted or unsubstituted C ₃ -C ₁₆ aryloxy cycloalkylene group, a substituted or unsubstituted C ₆ -C ₃₀ aryl-oxy group, a substituted or unsubstituted C ₇ -C ₄₀ ahreu An alkylene group, a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group, -Si (Q ₄ ) (Q ₅ ) - and -N (Q ₄ ) -;
n5 is selected from 1, 2, 3, 4 and 5;
m2 is an integer from 0 to 20;
Q ₁ to Q ₅ are each independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₆ -C ₃₀ aryl group;

Of the above formulas (5-1) to (5-10)
R ₁₀ to R ₁₆ are, independently from each other, a hydrogen atom or a substituted or unsubstituted C ₁ -C ₂₀ alkyl group;
p is an integer from 1 to 10;
* Is the binding site with neighboring atoms. 16. The method of claim 15,
(A ') _n5 represents a single bond, a C ₁ -C ₂₀ alkylene group, a C ₆ -C ₃₀ arylene group and a group represented by the following formula (2); And
A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; Aminofluorene < / RTI > polymer:
(2)

In Formula 2,
L ₁ and L ₂ are, independently of each other, a single bond, a C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group; And
A C ₁ -C ₂₀ alkylene group and a C ₆ -C ₃₀ arylene group substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₃₀ aryl group; ;
n3 and n4 are independently from each other selected from 1 and 2;
Ar ₁ represents a hydrogen atom, a C ₁ -C ₂₀ alkyl group, and a C ₆ -C ₃₀ aryl group; And
C ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl group and C ₁ -C ₂₀ alkoxy at least one substituted, C ₆ -C ₃₀ aryl group selected from the group; ;
* Is the binding site with neighboring atoms. 15. The method of claim 14,
Wherein said second repeating unit is selected from the following structures: Aminofluorene polymer:

Among the above formulas,
n and m are, independently of each other, an integer of 1 to 10; A first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode;
Wherein the organic layer comprises the aminofluorene polymer of any one of claims 1 to 17. 19. The method of claim 18,
Wherein the organic layer comprises a light emitting layer;
Wherein the light emitting layer comprises a phosphorescent dopant. 19. The method of claim 18,
Wherein the organic layer comprises a hole transporting layer;
Wherein the aminofluorene polymer is included in the hole transport layer.

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