JP2008195761A - Polymer compound and organoelectroluminescent element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a positive hole-transporting polymer compound having high electron-blocking capability and to enhance emission efficiency and reliability of an organoelectroluminescent element by using the polymer compound. <P>SOLUTION: The polymer compound bearing a unit X represented by formula (1) and a unit A containing in its main chain a charge transporting molecule or a light-emitting molecule is used as the positive hole transporting material. The organoelectroluminescent element has such a constitution that the positive hole transporting layer or the light-emitting layer contains the material. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a hole transporting polymer compound and an organic electroluminescence (EL) device using the same.

  Since a display using an organic EL element uses an organic solid material having a thickness of several tens of nanometers as a light emitting material, a thin, light, and flexible display can be realized. In addition, since it is self-luminous, a high viewing angle is possible, and since the response speed of the light emitter itself is high, it is suitable for high-speed moving image display.

  Organic solid materials used for organic EL elements are roughly classified into low molecular weight systems and polymer systems. The polymer-based organic EL element can be applied to a printing method, an ink-jet method, and the like, and thus is suitable for mass productivity, cost reduction of a manufacturing process, and a large screen, and is expected.

  The organic EL element emits light by injecting holes from the anode and electrons from the cathode into the light emitting layer between the anode and the cathode, and recombining the electrons and holes in the light emitting layer. In a general organic EL device, in order to efficiently transport holes from the anode to the light emitting layer, a hole transport layer is provided between the anode and the light emitting layer, and similarly, an electron transport layer is provided between the cathode and the light emitting layer. By adopting a laminated structure in which is inserted, the drive voltage is reduced.

  Documents disclosing materials used for organic electroluminescence elements include the following Patent Documents 1 and 2.

  [0055] to [0059] of Patent Document 1 list materials used for a light emitting layer and a charge transport layer of an organic EL element.

  [0068] In Patent Document 2 [0068], in at least one of the organic layers of the organic EL element, a polymer compound containing a binding unit having a ligand function, an organometallic complex independent of the polymer compound, and It is described to contain.

Japanese Patent Laid-Open No. 2005-23072 JP 2004-319305 A

  In addition to efficiently transporting holes to the light-emitting layer, the performance required for the hole transport material of the organic EL element is to block electrons that pass through the anode as they are without emitting light in the light-emitting layer. By blocking the electrons, the electrons are confined in the light emitting layer, and the light emission efficiency can be increased.

Further, when electrons reach the anode from the light emitting layer, the electrons attack the PEDOT (poly (3,4-ethylenedioxythiophene))-PSS (polystyrene sulfonic acid) film or ITO (indium tin oxide) film constituting the anode. As a result, it has been found that the deterioration of the device proceeds. For this reason as well, increasing the electron blocking performance in the hole transport layer is an important issue not only for improving the light emission efficiency but also for improving the reliability of the device.

  Patent Documents 1 and 2 do not select a material for hole transport from such a viewpoint, and do not disclose an optimal compound configuration.

  An object of the present invention is to provide a hole transporting polymer compound having a large electron blocking ability. Furthermore, there exists in improving the luminous efficiency and reliability of an organic electronic luminescent element by using this polymer compound for a positive hole transport layer.

  In order to solve the above-described problems, the present invention takes a configuration of a polymer compound that includes a unit X represented by the formula (1) and a unit A having a charge transporting molecule or a light emitting molecule in the main chain.

(Wherein n is an integer of 3 or more and 7 or less, X _i (i is an integer of 1 or more and n or less) represents a carbon or nitrogen atom, and X _{1 to} X _n are at least one of carbon and nitrogen. In the above, adjacent X _i are linked by a single bond, and polymerize at the X ₁ position and X _k position (k is an integer of 2 or more and n or less) as the main chain of the polymer compound. The substituent R may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a straight chain having 1 to 22 carbon atoms, A cyclic or branched alkyl group or a halogen-substituted alkyl group in which a part or all of hydrogen atoms thereof are substituted, an aryl group having 6 to 21 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, or 7 to 21 carbon atoms Aralkyl groups of them Halogen-substituted aryl group partially or fully substituted with halogen atoms of the hydrogen atom, heteroaryl group halogen substituted, a halogen-substituted aralkyl group. In addition, the X _i which is not directly attached chemical through a substituent R It may be bound to
In addition, the unit X has a polymer compound structure represented by any one of formulas (2) to (7).

(In the formula, Ra and Rb are the same as the substituent R described above, and a plurality of Ras may be present,
When there are a plurality of Ras, they may be different from each other. )
Further, the unit X has a configuration of an organic polymer compound represented by the formula (8) or the formula (9).

(X ′ in the formula represents either the above formula (1) or the above formulas (2) to (7). Rc, Rd, and Re are the same as the above-described substituent R, The polymer compound may be different from each other in the case of having a plurality of polymer compounds, and the unit A having a charge transporting or light-emitting molecule separately defined from the unit X having the saturated cyclic amine may be used. And may be a homopolymer or copolymer of the formula (8) or (9).
Further, the unit A has a structure of a polymer compound having a conjugated structure.

(However, each of the unit A and the unit X may have a plurality of components.)
Further, the unit A takes the configuration of a polymer compound represented by the formula (10).

(In the formula, R is the same as the substituent R described above.)
Furthermore, in the organic electroluminescence device having an anode, a cathode, a light emitting layer disposed between the anode and the cathode, and a hole transport layer disposed between the anode and the light emitting layer, The hole transport layer or the light emitting layer is configured to contain the polymer compound described above.

  According to the present invention, a hole transporting polymer compound having a larger electron blocking ability than that of a conventional material can be obtained. By using this polymer compound for an organic EL device, it is possible to prevent electrons from reaching the anode, so that light emission efficiency and device reliability are improved.

  Hereinafter, the best mode for carrying out the present invention will be described.

First, [Configuration of organic electroluminescence device], [Molecular orbital method based on density functional method], [Dependence of luminous efficiency on hole transporting polymer], and [Synthesis method of polymer compound], which are the premise of Examples Will be described, followed by examples.
[Configuration of organic electroluminescence element]
FIG. 1 shows a stacked structure of organic electroluminescence elements on the horizontal axis and the energy level on the vertical axis.

  As shown on the horizontal axis of FIG. 1, examples of the organic electroluminescence element include a laminated structure of an anode, a hole transport layer, a light emitting layer, and a cathode. Specific examples of the configuration in this case include the following, for example. The anode is composed of a film obtained by spin-coating PSS (polystyrene sulfonic acid) and PEDOT (poly (3,4-ethylenedioxythiophene)) on a glass substrate patterned with ITO (indium tin oxide). As the hole transport layer and the light emitting layer, a polymer compound is formed with a thickness of about several to several tens of nm by a coating process or the like. However, the light emitting layer may exist independently of the polymer compound and may be doped with a light emitter responsible for light emission. The cathode is composed of a film in which a LiF or Ba film is stacked on the light emitting layer by several nm, and Al is stacked thereon by about 100 nm. Furthermore, an electron transport layer may be laminated between the light emitting layer and the cathode. As other forms, there are a laminated structure in which a charge transport layer or the like is further added to FIG. 1, a structure having only a single light emitting layer between the anode and the cathode, and a top emission type structure in which the cathode is a transparent electrode.

  The vertical axis | shaft of FIG. 1 shows the energy level of the electron and hole in an organic EL element. The HOMO (Highest Occupied Molecular Orbital) level in the figure is the energy necessary for injecting holes into each layer, and is obtained by reversing the sign of the ionization energy of the material constituting the layer. . The LUMO (Lowest Unoccupied Molecular Orbital) level is energy for injecting electrons into each layer and is obtained by reversing the sign of the electron affinity of the substance constituting the layer.

  Therefore, it can be seen that the smaller the electron affinity is, the higher the electron blocking performance is, and if the ionization energy is the same as that of the conventional material, a hole transport polymer having equivalent hole transport performance can be obtained.

  Based on the above, in one configuration of the present invention, regarding the polymer compound used as the hole transport layer on the horizontal axis in FIG. 1, the monomer unit constituting the polymer is replaced with the monomer unit containing the saturated cyclic amine according to the present invention. Alternatively, the polymer compound is replaced with the polymer compound containing the saturated cyclic amine according to the present invention.

The materials used for the hole transport layer and the synthesis method thereof will be described in detail below.
[Molecular orbital method based on density functional theory]
In Examples 1 to 5 described below, a conventional monomer unit or polymer compound is replaced with a monomer unit or polymer compound containing a saturated cyclic amine in the hole transport layer in the organic EL device shown in FIG. The molecular orbital calculation based on the density functional method shows that the electron blocking performance is improved by the monomer unit or polymer compound containing a saturated cyclic amine and has the same hole transport performance as the conventional one. Specifically, the ionization energy and electron affinity of the monomer unit or polymer compound according to the present invention and the polymer compound according to the present invention are calculated by the molecular orbital method based on the density functional method. It shows that the electron affinity is small, the electron blocking performance is improved, the ionization energy is the same as the conventional one, and the hole transport performance is the same as the conventional one. In Examples 1 to 5, it is mainly applied to a hole transport polymer in an organic EL device, but as shown in Example 6, it may be used for a light emitting layer polymer.

  This item shows the accuracy of the calculated values of ionization energy and electron affinity of the molecular orbital method based on the density functional method used in each example.

  Ionization energy and electron affinity were calculated as follows. As the density functional method, the usual local density approximation was adopted, and the valence double basis consisting of the slater type basis was used as the basis function, and the total energy of the molecule was obtained (molecular orbital method based on the density functional method). The detailed calculation method of the total energy of the molecule is described in, for example, K. Kobayashi, K. Tago, and N. Kurita, Phys. Rev. A, 53, 1903 (1996)). The ionization energy and electron affinity were calculated from the difference between the total energy of the neutral state and the total energy of the charged state (+1 valence for the calculation of ionization energy and -1 valence for the calculation of electron affinity). In the calculation, an analysis system of 1 unit of the molecular structure was used for the monomer molecule. For polymer compounds, the ionization energy and electron affinity were calculated under an analytical system in which 2 and 4 monomer units were polymerized. The calculation result is plotted against x defined by x = 1 / number of monomer units, and the intercept obtained by extrapolating the calculation result to x = 0 (that is, infinite number of monomer units) is defined as the ionization energy or electron affinity of the polymer. .

  Table 1 shows a comparison between the calculation results of ionization energy ([eV]) and electron affinity ([eV]) and measured values in the gas phase for typical organic molecules (naphthalene, fluorine, pyrene, azulene). .

  Table 1 shows that for each organic molecule, the calculated value and the measured value agree within an error of 0.1 eV.

From the above, it was confirmed that the ionization energy and electron affinity of the monomer molecule or polymer compound can be evaluated from the molecular orbital method based on the density functional method.
[Dependence of luminous efficiency on hole transport polymer]
In the above item [Structure of organic electroluminescence element], based on the energy diagram of the organic EL element, it was shown that the electron blocking performance increases as the electron affinity decreases. In this item, the influence of the hole transport layer polymer compound on the luminous efficiency of the organic EL device was investigated.

  The element configuration and production method of the organic EL actually measured are shown below.

An aqueous solution in which PSS (polystyrene sulfonic acid) and PEDOT (poly (3,4-ethylenedioxythiophene)) are colloidally dispersed at a weight ratio of 20: 1 on a glass substrate patterned with ITO (indium tin oxide). The film coated with spin is used as the anode. Thereafter, a polymer compound TPA-FO8 or TPAMe-FO8 is laminated as a hole transport layer by a coating process to a thickness of 30 nm. As the light emitting layer, polymer compound PFO /
TPA-FO is laminated by 50 nm by a coating process. On top of this, 2 nm of Ba and 150 nm of metal Al are deposited as a cathode electrode layer.

(Chemical ratio 2-1)

(Chemical ratio 2-2)

PFO8 / 2TPA-FO is a mixture of polymer compounds, PFO8 and 2TPA-
FO is mixed at a weight ratio of 8: 2.

  The ionization energy and electron affinity of the hole transport layer polymer compounds TPA-FO8, TPAMe-FO8 and PFO8 which is the main component of the light emitting layer polymer compound were calculated.

  Table 2 shows the results of experiments and calculations.

  Measured value of luminous efficiency ([cd / A]), ionization energy (IE), electron affinity (EA), hole transport for each case where the hole transport layer is TPA-FO8 and TPAMe-FO8. The calculated value (eV) of the difference in electron affinity (ΔEA) between the layer polymer and the light emitting layer polymer PFO8 was determined. The organic EL elements were all produced under the same conditions except that the polymer of the hole transport layer was different.

As a result, it was found that the light emission efficiency of the device using TPAMe-FO8 was higher than that of TPA-FO8. The ionization energies of TPA-FO8 and TPAMe-FO8 coincide with each other with a difference of 0.01 eV, and the hole transport ability is equivalent. On the other hand, the electron affinity of TPAMe-FO8 is 0.2 or more smaller than that of TPA-FO8. This indicates that the TPAMe-FO8 is difficult to inject electrons and has a high blocking performance. The difference ΔEA from the electron affinity of PFO8 increases from 0.19 to 0.42 eV, and the energy barrier of electrons between the light emitting layer and the hole transport layer increases. This corresponds to the fact that the measured value of the luminous efficiency is higher in TPAMe-FO8.

From the above results, it was confirmed that the luminous efficiency is increased by using a polymer compound that gives a small electron affinity value for the hole transport layer.
[Synthesis Method of Polymer Compound]
In the present invention, a polymer compound containing a saturated cyclic amine is used as the hole transport layer of the organic EL device. In this section, a method for synthesizing a polymer containing a saturated cyclic compound will be described.

  A polymer containing a saturated cyclic compound can be synthesized by a known synthesis technique and a combination thereof. For example, for aryl groups and amines, a method using a copper catalyst or sodium-tert-butoxide as a base, bis (bisdibenzylideneacetone) -bis (tri-o-tolylphosphine) palladium or dichlorobis (tri-o -Triphosphine) can be bonded by using a palladium compound catalyst. It is possible to polymerize saturated cyclic amines and conjugated groups such as phenyl groups and fluorenes by optimizing synthesis methods, synthesis conditions, and catalysts.

  In addition, when a molecule in which a conjugated molecule such as a saturated cyclic amine and a phenyl group is bonded is used as a monomer unit, a Suzuki coupling method can be used. For example, by adding Br or boronic acid to 1,4 diphenylpiperazine, it is possible to synthesize a polymer compound containing a saturated cyclic amine as shown in the following (Compound 1) and (Compound 2).

(Compound 1)

(Compound 2)

[Configuration of each embodiment]
Based on the above-described items, Example 1-6 will be described below.

  In Examples 1 to 6, cases where piperazine is used as a unit having a saturated cyclic amine and fluorene is used as a charge transport or light emitting unit will be described, but the present invention is not limited to polymer compounds using these units. Absent. As the saturated cyclic amine, a unit containing any one of ethyleneamine, azetidine, piperazine, pyridazine, piperidine, pyrrolidine, pyrazolidine, homopiperazine, and hexamethyleneimine may be used.

Further, the charge transport or light emitting unit may be a unit represented by a monomer unit that has been used in a known organic EL charge transport layer or light emitting layer, such as triphenylamine, arylamine derivatives, triphenylmethane derivatives, Stilbene compounds, hydrazone compounds, carbazole compounds, arylamines, anilines, thiophenes, oxadiazole derivatives, benzoxazole derivatives, benzoquinone derivatives, quinoline derivatives, quinoxaline derivatives, thiadiazole derivatives, benzodiazole derivatives, triazole derivatives, arylamines Derivatives, oxadiazole derivatives, perylene derivatives, quinacridone derivatives, pyrazoline derivatives, anthracene derivatives, rubrene derivatives, stilbene derivatives, coumarin derivatives, naphthalene derivatives , Benzene, biphenyl, terphenyl, naphthalene, anthracene, tetracene, fluorene, phenanthrene, pyrene, chrysene, pyridine, pyrazine, quinoline, isoquinoline, acridine, phenanthroline, furan, pyrrole, thiophene, oxazole, oxadiazole, thiadiazole, triazole, Benzoxazole, benzooxadiazole, benzothiadiazole, benzothiophene, N- (4-butylphenyl) -N-diphenylamine, N, N′-diphenyl-N,
N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine, N, N'-bis (3-methylphenyl) -N, N'-bis (2-naphthyl) )-[1,1′-biphenyl] -4,4′-diamine, which may contain a plurality of components in the main chain.

Saturated cyclic amine monomer unit The hole transporting monomer unit of the conventional organic EL polymer compound is replaced with a saturated cyclic amine monomer unit. The following compounds were examined as hole transporting monomer units of conventional organic EL polymer compounds.

(Chemical 1-1)

  Moreover, the following compounds were examined as a monomer unit of a saturated cyclic amine.

(Chemical 1-2)

  Table 3 shows the results of the study.

  Triphenylamine TPA and fluorene FO8 are known to exhibit good hole transport performance. These are units having negative electron affinity and are difficult to inject electrons, but their absolute value is 0.1 eV or less and the blocking performance is low.

  The electron affinity of cyclohexane is -1.8 eV, and electrons are less likely to be injected than TPA and FO. For this reason, high electron blocking performance is given. However, the ionization energy is 1.0 eV or more higher than that of TPA and FO, and is not easily ionized. This indicates that cyclohexane acts as a bulky or spacer unit in the polymer as shown in Japanese Patent Application No. 2004-48590, but the hole transport performance is inferior.

  On the other hand, the ionization energy of the unit having a saturated cyclic amine is equivalent to FO8, and the electron affinity is equivalent to cyclohexane. From this, it was shown that the hole transport performance is secured with the saturated cyclic amine and the electron blocking performance is improved.

Monomer unit of saturated cyclic amine with adjacent conjugated group Hole transportable monomer units TPA, FO, piperazine of Example 1 piperazine in which piperazine represented by the following formula and conjugated molecule phenyl or fluorene are adjacently bonded Replace with compound unit.

(Chemical fruit 2)

  The results are shown in Table 4.

  PPZa to PPZd all have negative electron affinity, and their absolute values are as large as 0.4 eV or more. Compared to piperazine, the electron blocking performance was improved compared to TPA and FO, although it was slightly inferior. Moreover, the hole transport performance is equivalent to that of TPA. From the above, it was found that a hole transport material having electron blocking performance higher than that of a conventional material can be provided even in a compound unit in which a phenyl group is adjacent to piperazine, regardless of the bonding position of the phenyl group. It was also found that the same effect as the phenyl group can be obtained in the unit adjacent to fluorene.

Saturated cyclic amine monomer unit for Suzuki coupling synthesis method In the PPZa to PPZd, a compound in which -Br and boronic acid are polymerized on a phenyl group as shown in the following formula can be synthesized.

(Chemical fruit 3)

  By using these compounds, the Suzuki coupling synthesis method can be applied, and a polymer containing a saturated cyclic amine can be produced in a high yield.

Polymer compounds containing saturated cyclic amines The following polymer PPZ-FO consisting of piperazine units which are saturated cyclic amines and luminescent and hole transporting fluorene units, and conventional hole transporting polymers TPA-FO and TPAMe-FO Compared.

(Chemical 4-1)

(Chemical 4-2)

  Table 5 shows the results.

  Compared to TPA-FO8 and TPAMe-FO8, the ionization energy of PPZ-FO8 is only 0.15, and PPZ-FO8 has the same hole transport performance as TPA-FO8 and TPAMe-FO8. Indicated. On the other hand, PPZ-FO8 has an electron affinity of 0.7 eV or more smaller than TPA-FO8 and TPAMe-FO8, indicating that the electron blocking performance is dramatically improved. From the above, by using a polymer compound having a saturated cyclic amine, hole transport performance was secured and electron blocking performance was improved.

Organic EL Device Using Polymer Compound Containing Saturated Cyclic Amine An example of an organic EL device structure when a polymer compound containing a saturated cyclic amine is used as the hole transport layer is shown below. An aqueous solution in which PSS (polystyrene sulfonic acid) and PEDOT (poly (3,4-ethylenedioxythiophene)) are colloidally dispersed at a weight ratio of 20: 1 on a glass substrate patterned with ITO (indium tin oxide). The film coated with spin is used as the anode.

Thereafter, a saturated cyclic amine PPZ-FO is laminated as a hole transporting layer with a thickness of 30 nm by any one of the above-described methods for synthesizing the polymer compound. As the light emitting layer, for example, a polymer compound PFO8 / 2TPA-FO8 is laminated by 50 nm by a coating process. On top of this, 2 nm of Ba and 100 nm of metal Al are deposited as a cathode electrode layer. Further, a device in which TPAMe-FO8 is stacked as a hole transport layer by spin coating with a thickness of 30 nm is used as a comparative example.

  FIG. 2 shows an energy diagram between the hole transport layer and the light emitting layer when (a) TPAMe-FO is used as the hole transport layer and (b) PPZ-FO is used. The HOMO and LUMO energy levels in the figure are values obtained by inverting the sign of ionization energy and electron affinity of each polymer. Comparing (a) and (b), the difference (barrier) between the hole transport layer and the light emitting layer at the HOMO energy level is about 0.4 to 0.5 eV in both cases, and PPZ-FO is TPAMe-FO. Has the same hole transport capability. Since TPAMe-FO is a good hole transport polymer, it can be seen that PPZ-FO is also a hole transport polymer having equivalent hole transport performance. In contrast, the LUMO energy level of TPA-Me has only a 0.42 eV barrier, whereas PPZ-FO has a 1.15 eV barrier, which indicates that PPZ-FO has a high electron blocking performance. . Therefore, PPZ-FO functions as a good hole transport material having high electron blocking performance in the organic EL element.

  Organic EL device using saturated cyclic amine polymer compound as light-emitting layer matrix

  FIG. 3 shows a device structure in the case where a polymer compound containing a saturated cyclic amine typified by piperazine is used for the light emitting base material of the light emitting layer. The light emitting layer is formed of a light emitting base material that is a main substance forming the layer and a light emitting material that is responsible for light emission. The energy level represented by the line over the entire light emitting layer in FIG. 3 is the energy level of the light emitting base material, and the energy level represented by the short line in the light emitting layer is the energy level of the light emitter. Electrons and holes are respectively injected from the cathode and the anode into the light-emitting base material, and after electrons and holes move from the light-emitting base material to the light-emitting body, they recombine and emit light.

  A polymer compound containing a saturated cyclic amine typified by piperazine has a property of blocking holes and transporting holes, and is therefore more suitable for transporting holes to a light emitter more preferentially. The above properties are more conspicuous as the content of the saturated cyclic amine in the polymer compound is larger. Therefore, by adjusting the content, the balance between electrons and holes in the light emitting layer can be adjusted. For example, under device conditions in which electrons are excessively injected into the light emitting layer, the amount of injected electrons is reduced by increasing the content of the saturated cyclic amine.

Energy diagram of organic EL device. Energy diagram between the hole transport layer and the light emitting layer. Energy diagram of organic EL device.

Claims (18)

A unit X represented by the formula (1);
A polymer compound comprising a unit A having a charge transporting molecule or a light emitting molecule in the main chain.

(Wherein n is an integer of 3 or more and 7 or less, X _i (i is an integer of 1 or more and n or less) represents a carbon or nitrogen atom, and X _{1 to} X _n are at least one of carbon and nitrogen. In the above, adjacent X _i are linked by a single bond, and polymerize at the X ₁ position and X _k position (k is an integer of 2 or more and n or less) as the main chain of the polymer compound. The substituent R may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a straight chain having 1 to 22 carbon atoms, A cyclic or branched alkyl group or a halogen-substituted alkyl group in which a part or all of hydrogen atoms thereof are substituted, an aryl group having 6 to 21 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, or 7 to 21 carbon atoms Aralkyl groups of them Halogen-substituted aryl group partially or fully substituted with halogen atoms of the hydrogen atom, heteroaryl group halogen substituted, a halogen-substituted aralkyl group. In addition, the X _i which is not directly attached chemical through a substituent R It may be bound to The polymer compound according to claim 1, wherein the unit X is any one of formulas (2) to (7).

(In the formula, Ra and Rb are the same as the substituent R described in claim 1, and a plurality of Ras may be present, and when a plurality of Ras are present, they may be different from each other.) The organic polymer compound according to claim 1, wherein the unit X is represented by either formula (8) or formula (9).

(X ′ in the formula represents any one of the formula (1) described in claim 1 or formulas (2) to (7) described in claim 2. Rc, Rd, and Re represent the substitution described in claim 1. It is the same as the group R, and it may have a plurality, and if it has a plurality, it may be different from each other.The polymer compound is a charge transport property or light emission separately defined from the unit X having a saturated cyclic amine of claim 1. (The unit A having a sex molecule may not be present, and may be a homopolymer or a copolymer comprising the formula (8) or (9).) The polymer compound according to claim 1, wherein the unit A has a conjugated structure.
(However, each of the unit A and the unit X may have a plurality of components.) The polymer compound according to claim 1, wherein the unit A is the formula (10).

(In the formula, R is the same as the substituent R described in claim 1.) The polymer compound according to claim 2, wherein the unit A is the formula (10).

(In the formula, R is the same as the substituent R described in claim 1.) The polymer compound according to claim 3, wherein the unit A is the formula (10).

(In the formula, R is the same as the substituent R described in claim 1.) The polymer compound according to claim 4, wherein the unit A is the formula (10).

(In the formula, R is the same as the substituent R described in claim 1.) An anode, a cathode, a light-emitting layer disposed between the anode and the cathode, and a hole transport layer disposed between the anode and the light-emitting layer,
The hole transport layer is
An organic electroluminescence device having a polymer compound containing a unit X represented by the formula (1) and a unit A having a charge transport molecule in a main chain.

(Wherein n is an integer of 3 or more and 7 or less, X _i (i is an integer of 1 or more and n or less) represents a carbon or nitrogen atom, and X _{1 to} X _n are at least one of carbon and nitrogen. In the above, adjacent X _i are linked by a single bond, and polymerize at the X ₁ position and X _k position (k is an integer of 2 or more and n or less) as the main chain of the polymer compound. The substituent R may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a straight chain having 1 to 22 carbon atoms, A cyclic or branched alkyl group or a halogen-substituted alkyl group in which a part or all of hydrogen atoms thereof are substituted, an aryl group having 6 to 21 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, or 7 to 21 carbon atoms Aralkyl groups of them Halogen-substituted aryl group partially or fully substituted with halogen atoms of the hydrogen atom, heteroaryl group halogen substituted, a halogen-substituted aralkyl group. In addition, the X _i which is not directly attached chemical through a substituent R It may be bound to The organic electroluminescence element according to claim 9, wherein the unit X is any one of formulas (2) to (7).

(In the formula, Ra and Rb are the same as the substituent R described in claim 1, and a plurality of Ras may be present, and when a plurality of Ras are present, they may be different from each other.) The organic electroluminescent element according to claim 9, wherein the unit X is either formula (8) or formula (9).

(X ′ in the formula represents any one of the formula (1) described in claim 1 or formulas (2) to (7) described in claim 2. Rc, Rd, and Re represent the substitution described in claim 1. It is the same as the group R, and it may have a plurality, and if it has a plurality, it may be different from each other.The polymer compound is a charge transport property or light emission separately defined from the unit X having a saturated cyclic amine of claim 1. (The unit A having a sex molecule may not be present, and may be a homopolymer or a copolymer comprising the formula (8) or (9).) The organic electroluminescence device according to claim 9, wherein the unit A has a conjugated structure.
(However, each of the unit A and the unit X may have a plurality of components.) The organic electroluminescence element according to claim 9, wherein the unit A is Formula (10).

(In the formula, R is the same as the substituent R described in claim 1.) An anode, a cathode, and a light-emitting layer disposed between the anode and the cathode,
The light emitting layer is
An organic electroluminescence device having a polymer compound containing a unit X represented by formula (1) and a unit A having a luminescent molecule in the main chain.

(Wherein n is an integer of 3 or more and 7 or less, X _i (i is an integer of 1 or more and n or less) represents a carbon or nitrogen atom, and X _{1 to} X _n are at least one of carbon and nitrogen. In the above, adjacent X _i are linked by a single bond, and polymerize at the X ₁ position and X _k position (k is an integer of 2 or more and n or less) as the main chain of the polymer compound. The substituent R may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a straight chain having 1 to 22 carbon atoms, A cyclic or branched alkyl group or a halogen-substituted alkyl group in which a part or all of hydrogen atoms thereof are substituted, an aryl group having 6 to 21 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, or 7 to 21 carbon atoms Aralkyl groups of them Halogen-substituted aryl group partially or fully substituted with halogen atoms of the hydrogen atom, heteroaryl group halogen substituted, a halogen-substituted aralkyl group. In addition, the X _i which is not directly attached chemical through a substituent R It may be bound to The organic electroluminescent element according to claim 14, wherein the unit X is any one of formulas (2) to (7).

(In the formula, Ra and Rb are the same as the substituent R described in claim 1, and a plurality of Ras may be present, and when a plurality of Ras are present, they may be different from each other.) The organic electroluminescent element according to claim 14, wherein the unit X is represented by formula (8) or formula (9).

(X ′ in the formula represents any one of the formula (1) described in claim 1 or formulas (2) to (7) described in claim 2. Rc, Rd, and Re represent the substitution described in claim 1. It is the same as the group R, and it may have a plurality, and if it has a plurality, it may be different from each other.The polymer compound is a charge transport property or light emission separately defined from the unit X having a saturated cyclic amine of claim 1. (The unit A having a sex molecule may not be present, and may be a homopolymer or a copolymer comprising the formula (8) or (9).) The organic electroluminescence device according to claim 14, wherein the unit A has a conjugated structure.
(However, each of the unit A and the unit X may have a plurality of components.) The organic electroluminescent element according to claim 14, wherein the unit A is formula (10).

(In the formula, R is the same as the substituent R described in claim 1.)

Images