Polymer and organic light emitting device using the same

Abstract

This specification relates to polymers and organic light emitting devices formed by using them.

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2021-0180872, filed with the Korean Intellectual Property Office on December 16, 2021, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to polymers and organic light-emitting devices formed using them. Background Technology

[0003] Organic light emission is one example of converting electric current into visible light through internal processes of specific organic molecules. The principle of organic light emission is as follows: When an organic material layer is placed between a positive and a negative electrode, if a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the negative and positive electrodes, respectively. The injected electrons and holes recombine to form excitons, which then fall back to the ground state to emit light. Organic electroluminescent devices using this principle typically consist of a negative electrode, a positive electrode, and an organic material layer disposed therebetween (e.g., an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer).

[0004] The materials used in organic light-emitting devices are mainly pure organic materials or complex compounds in which organic materials and metals form complexes. Based on their applications, they can be classified as hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injection materials. In this paper, organic materials with p-type characteristics (i.e., organic materials that are easily oxidized and have an electrochemically stable state during oxidation) are typically used as hole injection or hole transport materials. Simultaneously, organic materials with n-type characteristics (i.e., organic materials that are easily reduced and have an electrochemically stable state during reduction) are typically used as electron injection or electron transport materials. As luminescent materials, materials possessing both p-type and n-type characteristics are preferred (i.e., materials that are stable in both oxidized and reduced states), and materials with high luminescent efficiency for converting excitons into light when excitons are formed are also preferred.

[0005] In addition to those mentioned above, it is preferable that the materials used in organic light-emitting devices also have the following properties.

[0006] First, it is preferable that the materials used in organic light-emitting devices (OLEDs) possess excellent thermal stability. This is because Joule heating occurs due to the movement of charges within the OLED. Currently, the glass transition temperature of N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), which is commonly used as a hole transport material, is 100°C or lower, making it difficult to use in OLEDs requiring high currents.

[0007] Second, to obtain high-efficiency organic light-emitting devices (OLEDs) that can be driven at low voltages, it is necessary to facilitate the transfer of holes or electrons injected into the OLED to the emissive layer, while simultaneously preventing the released holes and electrons from the emissive layer. For this purpose, the materials used in OLEDs need to have appropriate band gaps and appropriate highest occupied molecular orbitals (HOMO) or lowest unoccupied molecular orbitals (LUMO) energy levels. Because poly(3,4-ethylenedioxythiophene)-doped poly(styrene sulfonic acid) (PEDOT:PSS), currently used as the hole transport material in OLEDs to be manufactured via solution application, has a lower LUMO energy level than the organic materials used as the emissive layer material, it is difficult to manufacture OLEDs with high efficiency and long lifespan.

[0008] Furthermore, materials used in organic light-emitting devices (OLEDs) need to possess excellent chemical stability, excellent charge mobility, and excellent interfacial properties with electrodes or adjacent layers. Specifically, the materials used in OLEDs need to minimize deformation caused by moisture or oxygen. Additionally, the materials used in OLEDs need to have appropriate hole or electron mobility to achieve a balance between the density of holes and electrons in the light-emitting layer of the OLED, thereby maximizing exciton formation. Moreover, for device stability, the materials used in OLEDs need to improve the interface with electrodes containing metals or metal oxides.

[0009] In addition to those mentioned above, the materials used in organic light-emitting devices for solution processing need to have the following additional properties.

[0010] First, the materials used in organic light-emitting devices need to form a storable homogeneous solution. Because commercially available materials used in deposition methods have good crystallinity, they cannot dissolve well in solution, or even if the material forms a solution, crystals tend to form easily, which may change the concentration gradient of the solution over time, or result in defective devices.

[0011] Second, the layer used in the solution process needs to be solvent-resistant and material-resistant to other layers. Therefore, materials that can form self-crosslinking polymers on the substrate by heat treatment or ultraviolet (UV) irradiation after the curing groups are introduced and the solution is applied, such as N4,N4'-di(naphthyl-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine (VNPB), or materials that can form polymers with sufficient resistance in subsequent processes, are preferred. Materials that are inherently solvent-resistant, such as hexaazabenzophenanthrene hexanitrile (HATCN), are also preferred.

[0012] Therefore, there is a need in this field to develop organic materials that meet the above requirements. Summary of the Invention

[0013] Technical issues

[0014] This specification is intended to provide polymers and organic light-emitting devices formed by using them.

[0015] Technical solution

[0016] An exemplary embodiment of this specification provides a polymer represented by the following chemical formula 1.

[0017] [Chemical Formula 1]

[0018] E1-[A1] a -[B1] b -[C1] c -E2

[0019] In chemical formula 1,

[0020] A1 is represented by the following chemical formula 2.

[0021] B1 is represented by the following chemical formula 3.

[0022] C1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0023] E1 and E2 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; crosslinkable group; or combinations thereof.

[0024] a, b, and c are each mole fractions.

[0025] a is a real number where 0 < a ≤ 1.

[0026] b is a real number where 0 ≤ b < 1.

[0027] c is a real number where 0 ≤ c < 1.

[0028] a+b+c=1,

[0029] [Chemical Formula 2]

[0030]

[0031] In chemical formula 2,

[0032] Ar1, Ar2, L1, and L2 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0033] R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0034] R10 to R13 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group.

[0035] n1 to n3 are each an integer from 1 to 4.

[0036] When n1 to n3 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and l1 and l2 are each integers from 1 to 5.

[0037] When l1 and l2 are each 2 or larger, the structures within each set of parentheses may be the same or different from each other.

[0038] * indicates a connection point in the polymer.

[0039] [Chemical Formula 3]

[0040]

[0041] In chemical formula 3,

[0042] m is an integer of 3 or 4.

[0043] When m is 3, Z is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group.

[0044] When m is 4, Z is C; Si; or a substituted or unsubstituted tetravalent aryl group.

[0045] Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0046] Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group.

[0047] When Y is a direct bond or a substituted or unsubstituted alkylene group, Z is a substituted or unsubstituted trivalent or tetravalent aryl group, and

[0048] * indicates a connection point in the polymer.

[0049] Another exemplary embodiment of this specification provides a polymer comprising a unit represented by the following chemical formula 2 and an end group represented by the following chemical formula 5.

[0050] [Chemical Formula 2]

[0051]

[0052] [Chemical Formula 5]

[0053] ＊ -[E]

[0054] In chemical formulas 2 and 5,

[0055] Ar1, Ar2, L1, and L2 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0056] R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0057] R10 to R13 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group.

[0058] n1 to n3 are each an integer from 1 to 4.

[0059] When n1 to n3 are each 2 or greater, the substituents in each bracket may be the same or different from each other.

[0060] l1 and l2 are each integers from 1 to 5.

[0061] When l1 and l2 are each 2 or larger, the structures within each set of parentheses may be the same or different from each other.

[0062] E is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; crosslinkable group; or combinations thereof, and

[0063] * indicates a connection point in the polymer.

[0064] Another exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the polymer.

[0065] Beneficial effects

[0066] The polymer according to an exemplary embodiment of this specification comprises a branched alkyl-substituted unit of Formula 2. Therefore, the solubility of the polymer to be prepared is improved.

[0067] Furthermore, the polymer according to an exemplary embodiment of this specification can be applied to organic light-emitting devices to improve the performance and / or stability of the devices. Attached Figure Description

[0068] Figure 1 and Figure 2 This is a diagram illustrating the structure of an organic light-emitting device according to some exemplary embodiments of this specification.

[0069] 1: Base

[0070] 2: Anode

[0071] 3: Emissive layer

[0072] 4: Cathode

[0073] 5: Hole injection layer

[0074] 6: Hole transport layer

[0075] 7: Electron Injection and Transport Layer Detailed Implementation

[0076] This instruction manual will be described in more detail below.

[0077] This specification provides for polymers represented by the following chemical formula 1.

[0078] [Chemical Formula 1]

[0079] E1-[A1] a -[B1] b -[C1] c -E2

[0080] In chemical formula 1,

[0081] A1 is represented by the following chemical formula 2.

[0082] B1 is represented by the following chemical formula 3.

[0083] C1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0084] E1 and E2 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; crosslinkable group; or combinations thereof.

[0085] a, b, and c are each mole fractions.

[0086] a is a real number where 0 < a ≤ 1.

[0087] b is a real number where 0 ≤ b < 1.

[0088] c is a real number where 0 ≤ c < 1.

[0089] a+b+c=1,

[0090] [Chemical Formula 2]

[0091]

[0092] In chemical formula 2,

[0093] Ar1, Ar2, L1, and L2 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0094] R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0095] R10 to R13 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group.

[0096] n1 to n3 are each an integer from 1 to 4.

[0097] When n1 to n3 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and l1 and l2 are each integers from 1 to 5.

[0098] When l1 and l2 are each 2 or larger, the substituents in each bracket may be the same or different from each other.

[0099] * indicates a connection point in the polymer.

[0100] [Chemical Formula 3]

[0101]

[0102] In chemical formula 3,

[0103] m is an integer of 3 or 4.

[0104] When m is 3, Z is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group.

[0105] When m is 4, Z is C; Si; or a substituted or unsubstituted tetravalent aryl group.

[0106] Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0107] Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group.

[0108] When Y is a direct bond or a substituted or unsubstituted alkylene group, Z is a substituted or unsubstituted trivalent or tetravalent aryl group, and

[0109] * indicates a connection point in the polymer.

[0110] In one exemplary embodiment of this specification, the polymer containing chemical formula 2 comprises branched alkyl groups. Therefore, the solubility of the polymer to be prepared is improved compared to polymers containing straight-chain alkyl groups. When the device is manufactured by solution processing, the increased solubility forms an excellent thin film, thereby resulting in improved performance of the manufactured device. Specifically, the polymer may contain branched alkyl groups to exhibit stable drive voltage, improved efficiency, and / or long service life characteristics when applied to a device.

[0111] In one exemplary embodiment of this specification, the polydispersity index (PDI) of the polymer is from 1 to 10. Preferably, the molecular weight distribution of the polymer is from 1 to 5. More preferably, the molecular weight distribution of the polymer is from 1 to 4.

[0112] In this specification, the polydispersity index (PDI) is calculated using the following equation (1).

[0113] Equation (1): PDI = weight-average molecular weight (Mw) / number-average molecular weight (Mn)

[0114] A broad molecular weight distribution in a polymer refers to the distribution of molecules with a wide range of molecular weights, which means that the polymer is difficult to synthesize reproducibly. Therefore, the broader the molecular weight distribution, the lower the homogeneity of the polymer. That is, the closer the molecular weight distribution is to 1, the more uniform the prepared polymer will be.

[0115] In one exemplary embodiment of this specification, the molecular weight of the polymer is measured by gel permeation chromatography (GPC).

[0116] In this specification, when a component is positioned "on" another component, this includes not only the case where one component is in contact with another component, but also the case where there is another component between the two components.

[0117] In this specification, when a component “includes” a constituent element, unless otherwise specifically described, this does not mean that other constituent elements are excluded, but rather that other constituent elements may be included.

[0118] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there are no restrictions on the position to be substituted, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more are substituted, the two or more substituents can be the same or different from each other.

[0119] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium; halogen group; alkyl; cycloalkyl; alkoxy; aryloxy; amino; aryl; and heterocyclic group, substituted with two or more of the exemplified substituents linked together, or without substituents. For example, "substituents linked with two or more substituents" can be biphenyl. That is, biphenyl can also be aryl and can be interpreted as substituents linked with two phenyl groups.

[0120] Examples of substituents will be described below, but are not limited to.

[0121] Examples of halogen groups in this specification include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0122] In this specification, alkyl groups can be straight-chain or branched, and their number of carbon atoms is not particularly limited, but is preferably from 1 to 60. According to one exemplary embodiment, the number of carbon atoms in the alkyl group is from 1 to 30. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc.

[0123] In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably from 3 to 60. According to one exemplary embodiment, the number of carbon atoms in the cycloalkyl group is from 3 to 30. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0124] In this specification, alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, and n-decoxy.

[0125] In this specification, fluoroalkoxy means an alkoxy group substituted with F.

[0126] In this specification, the amino group may be selected from -NH2; alkylamino; arylalkylamino; arylamino; arylheteroarylamino; alkylheteroarylamino; and heteroarylamino, and is not limited thereto. The number of carbon atoms in the amino group is not particularly limited, but is preferably from 1 to 60.

[0127] In this specification, the number of carbon atoms in the aryl group is not particularly limited, but is preferably 6 to 60. According to one exemplary embodiment, the number of carbon atoms in the aryl group is 6 to 30. In one exemplary embodiment of this specification, the aryl group can be a monocyclic aryl or a polycyclic aryl. Specific examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0128] In this specification, arylene refers to a group having two bonding positions within an aryl group, i.e., a divalent group. The above description of aryl groups can be applied to arylene groups, the difference being that arylene groups are divalent.

[0129] In this specification, examples of arylamines include substituted or unsubstituted monoarylamines, substituted or unsubstituted diarylamines, or substituted or unsubstituted triarylamines. The aryl group in an arylamine can be a monocyclic aryl or a polycyclic aryl. An arylamine containing two or more aryl groups can include monocyclic aryl, polycyclic aryl, or both. For example, the aryl group in an arylamine can be selected from the above-described examples of aryl groups.

[0130] In this specification, a heterocyclic group comprises one or more atoms other than carbon (i.e., one or more heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30. In one exemplary embodiment of this specification, the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, and thiazolyl groups. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, phenthiazinyl, dibenzofuranyl, etc., but not limited to these.

[0131] In this specification, a divalent heterocycle can be monocyclic or polycyclic, and it means that there are two bonding sites in the heterocyclic group. Examples of divalent heterocyclic groups include divalent thiophene group; divalent carbazole group; divalent dibenzofuran group; divalent dibenzothiophene group, etc., but are not limited thereto.

[0132] In this specification, the aryloxy group is formed by -OR 200 The group represented, and R 200 It is an aryl group. The aryl group in aryloxy groups is the same as the aryl group mentioned above. Specific examples of aryloxy groups include phenoxy, benzyloxy, p-methylbenzyloxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc., but are not limited to these.

[0133] In this specification, silane is composed of -SiR 201 R 202 R 203 The group represented by R 201 R 202 and R 203 They may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0134] In this specification, siloxane is a compound formed by -Si(R) 204 )2OSi(R 205 )3 or -OSi(R 204 )3Si(R 205 )3 represents the group, R 204 and R 205They may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0135] In this specification, crosslinkable groups can refer to reactive substituents that crosslink a compound by exposure to heat, light, and / or radiation. Crosslinking can occur when free radicals generated by the decomposition of carbon-carbon multiple bonds and cyclic structures through heat treatment, light irradiation, and / or radiation irradiation connect with each other.

[0136] In one exemplary embodiment of this specification, the crosslinkable group is any of the following structures.

[0137]

[0138] In the structure, This refers to the portion that is bonded to another substituent or bonding portion.

[0139] In this specification, "adjacent" groups may mean a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, a substituent arranged spatially closest to the corresponding substituent, or another substituent that substitutes for the atom substituted by the corresponding substituent. For example, two substituents in the ortho position of a benzene ring and two substituents in an aliphatic ring that substitute for the same carbon atom can be interpreted as groups that are "adjacent" to each other.

[0140] In this specification, in a ring formed by bonding adjacent groups, "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0141] In this specification, "mole fraction" means the ratio of the number of moles of a given component to the total number of moles of all components.

[0142] In this specification, "combination of substituents" means a substituent in which two or more of the exemplified substituents are linked. For example, in hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, crosslinkable group, or combinations thereof, "combination" means a substituent in which two or more of the exemplified substituents are linked. As an example, the combination may have a structure in which an alkyl and a crosslinkable group are linked, or in which an alkyl and an aryl are linked, but is not limited thereto.

[0143] In one exemplary embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0144] In one exemplary embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0145] In one exemplary embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently phenylene; biphenylene; or naphthylene.

[0146] In one exemplary embodiment of this specification, chemical formula 2 is represented by the following chemical formula 2-1.

[0147] [Chemical Formula 2-1]

[0148]

[0149] In chemical formula 2-1,

[0150] R1 to R3, R10 to R13, Ar1, Ar2, and n1 to n3 are the same as those defined in Chemical Formula 2.

[0151] L3 and L4 may be identical or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group.

[0152] R15 and R16 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0153] n15 and n16 are each integers from 1 to 4.

[0154] When n15 and n16 are each 2 or greater, the substituents in each bracket may be the same or different from each other.

[0155] l3 and l4 are each integers from 1 to 4.

[0156] When l3 and l4 are each 2 or larger, the structures within each bracket may be the same or different from each other, and

[0157] * indicates a connection point in the polymer.

[0158] In one exemplary embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0159] In one exemplary embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted terphenylene.

[0160] In one exemplary embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently phenylene; biphenylene; or terphenylene.

[0161] In one exemplary embodiment of this specification, chemical formula 2 is represented by the following chemical formula 2-2.

[0162] [Chemical Formula 2-2]

[0163]

[0164] In chemical formula 2-2,

[0165] R1 to R3, R10 to R13, and n1 to n3 are the same as those defined in Chemical Formula 2.

[0166] R15 to R18 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0167] m1, m2, h1, and h2 are each integers from 1 to 3.

[0168] When m1, m2, h1, and h2 are each 2 or larger, the structures within each set of parentheses may be the same or different from each other.

[0169] n15 to n18 are each an integer from 1 to 4.

[0170] When n15 to n18 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and

[0171] * indicates a connection point in the polymer.

[0172] In one exemplary embodiment of this specification, chemical formula 2 is represented by the following chemical formulas 2-3.

[0173] [Chemical Formula 2-3]

[0174]

[0175] In chemical formula 2-3,

[0176] R10 to R13 are the same as those defined in Chemical Formula 2.

[0177] R1 to R3, R2', and R15 to R18 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0178] m1, m2, h1, and h2 are each integers from 1 to 3.

[0179] When m1, m2, h1, and h2 are each 2 or larger, the structures within each set of parentheses may be the same or different from each other.

[0180] n15 to n18 are each an integer from 1 to 4.

[0181] When n15 to n18 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and

[0182] * indicates a connection point in the polymer.

[0183] In one exemplary embodiment of this specification, chemical formula 2 is represented by the following chemical formulas 2-4 or 2-5.

[0184] [Chemical Formula 2-4]

[0185]

[0186] [Chemical Formula 2-5]

[0187]

[0188] In chemical formulas 2-4 and 2-5,

[0189] R10 to R13 are the same as those defined in Chemical Formula 2.

[0190] R1 to R3, R2', R15 to R18, R15' and R16' are the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; substituted or unsubstituted arylamino; or substituted or unsubstituted siloxane.

[0191] h1 and h2 are each integers from 1 to 3.

[0192] When h1 and h2 are each 2 or greater, the structures within each set of parentheses are either the same or different from each other, and n17 to n18 are each integers from 1 to 4.

[0193] When n17 to n18 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and

[0194] * indicates a connection point in the polymer.

[0195] In one exemplary embodiment of this specification, R1 to R3 are each hydrogen; deuterium; or substituted or unsubstituted alkyl groups.

[0196] In one exemplary embodiment of this specification, one or more of R1 to R3 are substituted or unsubstituted alkyl groups.

[0197] In one exemplary embodiment of this specification, any one of R1 to R3 is a substituted or unsubstituted alkyl group.

[0198] In one exemplary embodiment of this specification, both of R1 to R3 are substituted or unsubstituted alkyl groups.

[0199] In one exemplary embodiment of this specification, R1 to R3 are all substituted or unsubstituted alkyl groups.

[0200] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and one or more of R1 to R3 are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms.

[0201] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; or alkyl, and one or more of R1 to R3 are alkyl.

[0202] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; methyl; or hexyl, and one or more of R1 to R3 are methyl or hexyl.

[0203] In one exemplary embodiment of this specification, R1 and R3 are each methyl groups.

[0204] In one exemplary embodiment of this specification, R2 is hexylene.

[0205] In one exemplary embodiment of this specification, R2' is hexane.

[0206] In one exemplary embodiment of this specification, m1 and m2 are each 1 or 2.

[0207] In one exemplary embodiment of this specification, h1 and h2 are each 2.

[0208] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or substituted or unsubstituted alkyl groups.

[0209] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or alkyl.

[0210] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 30 carbon atoms.

[0211] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 10 carbon atoms.

[0212] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 5 carbon atoms.

[0213] In one exemplary embodiment of this specification, R15 to R18 may be the same as or different from each other, and each is independently hydrogen; or methyl.

[0214] In one exemplary embodiment of this specification, R15' and R16' may be the same as or different from each other, and each is independently hydrogen; or alkyl.

[0215] In one exemplary embodiment of this specification, R15' and R16' may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 30 carbon atoms.

[0216] In one exemplary embodiment of this specification, R15' and R16' may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 10 carbon atoms.

[0217] In one exemplary embodiment of this specification, R15' and R16' may be the same as or different from each other, and each is independently hydrogen; or an alkyl group having 1 to 5 carbon atoms.

[0218] In one exemplary embodiment of this specification, R15' and R16' may be the same as or different from each other, and each is independently hydrogen; or methyl.

[0219] In one exemplary embodiment of this specification, R10 to R13 are each alkyl groups.

[0220] In one exemplary embodiment of this specification, R10 to R13 are each alkyl groups having 1 to 10 carbon atoms.

[0221] In an exemplary embodiment of the present specification, each of R10 to R13 is methyl; ethyl; propyl; butyl; pentyl; or hexyl.

[0222] In an exemplary embodiment of the present specification, Chemical Formula 2 has the following structure.

[0223]

[0224] In said structure, * is a connection site in the polymer.

[0225] In an exemplary embodiment of the present specification, the unit represented by Chemical Formula 2 comprised in the polymer comprises a branched alkyl. Accordingly, an effect of improving uniformity of the polymer to be prepared is exhibited.

[0226] In an exemplary embodiment of the present specification, hydrogen may be substituted with deuterium. For example, hydrogen comprised in the structure may be substituted with deuterium.

[0227] In an exemplary embodiment of the present specification, a is a mole fraction, and is a real number satisfying 0 < a ≤ 1. That is, the polymer is required to comprise A1.

[0228] In an exemplary embodiment of the present specification, b is a mole fraction, and is a real number satisfying 0 ≤ b < 1. That is, the polymer optionally comprises B1.

[0229] In an exemplary embodiment of the present specification, b is a real number satisfying 0 < b < 1.

[0230] In an exemplary embodiment of the present specification, B1 in Chemical Formula 1 is a unit represented by Chemical Formula 3.

[0231] In an exemplary embodiment of the present specification, B1 is a unit having 3 or 4 connection sites.

[0232] In an exemplary embodiment of the present specification, Y is a direct bond; or a substituted or unsubstituted arylene.

[0233] In an exemplary embodiment of the present specification, Y is a direct bond; or a substituted or unsubstituted phenylene.

[0234] In an exemplary embodiment of the present specification, Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-1 to 3-4.

[0235] [Chemical Formula 3-1]

[0236]

[0237] [Chemical Formula 3-2]

[0238]

[0239] [Chemical Formula 3-3]

[0240]

[0241] [Chemical Formula 3-4]

[0242]

[0243] In chemical formulas 3-1 to 3-4,

[0244] Z1 is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group.

[0245] Z2 and Z3 may be identical or different from each other, and each is independently C; Si; or a substituted or unsubstituted tetravalent aryl group.

[0246] L10 is a direct bond; or a substituted or unsubstituted aryl group.

[0247] Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0248] R20 to R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; alkoxy; aryloxy; fluoroalkoxy; siloxane; substituted or unsubstituted amino group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or crosslinkable group, and adjacent groups may be bonded to each other to form a ring.

[0249] k1 is an integer from 1 to 4.

[0250] k2 is an integer from 1 to 5.

[0251] When k1 is 2 or greater, the substituents in parentheses may be the same or different from each other.

[0252] When k2 is 2 or greater, the substituents in parentheses are either the same or different from each other, and

[0253] * indicates a connection point in the polymer.

[0254] In one exemplary embodiment of this specification, chemical formula 3 is represented by chemical formula 3-1.

[0255] In one exemplary embodiment of this specification, Z1 is CRa or SiRa, and when Ra is a substituted or unsubstituted aryl group, L10 is a substituted or unsubstituted aryl group.

[0256] In one exemplary embodiment of this specification, Z1 is CH; SiH; N; or a substituted or unsubstituted trivalent aryl group.

[0257] In one exemplary embodiment of this specification, Z1 is CH; SiH; N; or a substituted or unsubstituted trivalent phenyl.

[0258] In one exemplary embodiment of this specification, Z1 is N; or trivalent phenyl.

[0259] In one exemplary embodiment of this specification, L10 is a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0260] In one exemplary embodiment of this specification, L10 is a direct bond; or an aryl group having 6 to 30 carbon atoms.

[0261] In one exemplary embodiment of this specification, L10 is a direct bond; or a phenylene oxide.

[0262] In one exemplary embodiment of this specification, L10 is a direct key.

[0263] In one exemplary embodiment of this specification, chemical formula 3 is represented by chemical formula 3-2.

[0264] In one exemplary embodiment of this specification, Z2 is C; or Si.

[0265] In one exemplary embodiment of this specification, chemical formula 3 is represented by chemical formula 3-3.

[0266] In one exemplary embodiment of this specification, Z3 is C; or Si.

[0267] In one exemplary embodiment of this specification, chemical formula 3 is represented by chemical formulas 3-4.

[0268] In one exemplary embodiment of this specification, chemical formula 3 is one of the following structures.

[0269]

[0270] In the structure,

[0271] R20 to R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; alkoxy; aryloxy; fluoroalkoxy; siloxane; substituted or unsubstituted amino group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or crosslinkable group, and adjacent groups may be bonded to each other to form a ring.

[0272] k1 is an integer from 1 to 4.

[0273] k2 is an integer from 1 to 5.

[0274] When k1 is 2 or greater, the substituents in parentheses may be the same or different from each other.

[0275] When k2 is 2 or greater, the substituents in parentheses are either the same or different from each other, and

[0276] * indicates a connection point in the polymer.

[0277] In one exemplary embodiment of this specification, R20 to R30 are each hydrogen.

[0278] Specifically, chemical formula 3 is any of the following structures.

[0279]

[0280] In the structure described, * represents a connection point in the polymer.

[0281] More specifically, chemical formula 3 is any of the following structures.

[0282]

[0283] In the structure described, * represents a bonding point in the polymer. More specifically, formula 3 is any of the following structures.

[0284]

[0285] In the structure described, * represents a connection point in the polymer.

[0286] In one exemplary embodiment of this specification, c is the mole fraction and is a real number where 0 ≤ c < 1. That is, the polymer selectively contains C1.

[0287] In one exemplary embodiment of this specification, C1 of chemical formula 1 is a unit with two connection points.

[0288] In one exemplary embodiment of this specification, C1 of Formula 1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0289] In one exemplary embodiment of this specification, C1 of Formula 1 is an unsubstituted or deuterated or crosslinkable aryl group; or an unsubstituted or deuterated or crosslinkable dicyclic group.

[0290] In one exemplary embodiment of this specification, C1 is any of the following structures.

[0291]

[0292] In the structure,

[0293] Y1 is S, O, or NR100.

[0294] R50 to R59 and R100 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or crosslinkable group.

[0295] k3 is an integer of 1 or 2.

[0296] k4 is an integer from 1 to 4.

[0297] k5 is an integer from 1 to 3.

[0298] k6 is an integer from 1 to 8.

[0299] When k3 to k6 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and

[0300] * indicates a connection point in the polymer.

[0301] Specifically, C1 is any of the following structures.

[0302]

[0303] In the structure,

[0304] Y1 is S, O, or NR100.

[0305] R50 to R59 and R100 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or crosslinkable group.

[0306] k3 is an integer of 1 or 2.

[0307] k4 is an integer from 1 to 4.

[0308] k5 is an integer from 1 to 3.

[0309] k6 is an integer from 1 to 8.

[0310] When k3 to k6 are each 2 or greater, the substituents in each bracket are either the same or different from each other, and

[0311] * indicates a connection point in the polymer.

[0312] More specifically, C1 is any of the following structures.

[0313]

[0314] In the structure described, * represents a connection point in the polymer.

[0315] In one exemplary embodiment of this specification, E1 and E2 are end-capping units of a polymer.

[0316] In one exemplary embodiment of this specification, E1 and E2 are units with only one connection point.

[0317] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a crosslinkable group; or a combination thereof.

[0318] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a crosslinkable group; or a combination thereof.

[0319] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a crosslinkable group; or a combination thereof.

[0320] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each is independently a crosslinkable group; or any of the following structures.

[0321]

[0322] In the structure,

[0323] R40 to R42 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; or crosslinkable group.

[0324] L40 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group.

[0325] i1 is an integer from 1 to 10.

[0326] j1 and j3 are each integers from 1 to 5.

[0327] j2 is an integer from 1 to 4.

[0328] When i1 is 2 or greater, two or more L40s are either the same or different from each other.

[0329] When j1 to j3 are each 2 or larger, the substituents in each bracket are either the same or different from each other, and

[0330] * indicates a connection point in the polymer.

[0331] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each independently represents any of the following structures.

[0332]

[0333] In the structure,

[0334] R40 to R42, L40, i1, j1 to j3 and * are as described above.

[0335] In one exemplary embodiment of this specification, R40 to R42 may be the same as or different from each other, and each is independently hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; or a crosslinkable group.

[0336] In one exemplary embodiment of this specification, L40 is a direct bond; an alkylene group having 1 to 10 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0337] In one exemplary embodiment of this specification, E1 and E2 may be the same as or different from each other, and each independently represents any of the following structures.

[0338]

[0339] In the structure described, * represents a connection point in the polymer.

[0340] More specifically, E1 and E2 are the same as or different from each other, and each is independently any of the following structures.

[0341]

[0342] In the structure described, * represents a connection point in the polymer.

[0343] In one exemplary embodiment of this specification, a, b, and c are determined by the equivalence ratio of the monomers used to prepare the polymer.

[0344] In one exemplary embodiment of this specification, a is a real number of 0.2 or greater.

[0345] In one exemplary embodiment of this specification, a is a real number from 0.2 to 1.

[0346] In one exemplary embodiment of this specification, a is a real number from 0.2 to 0.9.

[0347] In one exemplary embodiment of this specification, b is a real number of 0 or greater.

[0348] In one exemplary embodiment of this specification, b is a real number from 0 to 0.5.

[0349] In one exemplary embodiment of this specification, b is a real number greater than 0 and 0.5 or less.

[0350] In one exemplary embodiment of this specification, b is a real number from 0.1 to 0.4.

[0351] In one exemplary embodiment of this specification, c is a real number from 0 to 0.2.

[0352] In one exemplary embodiment of this specification, c is a real number from 0 to 0.1.

[0353] In one exemplary embodiment of this specification, c is 0.

[0354] In one exemplary embodiment of this specification, a is a real number from 0.3 to 1, b is a real number from 0 to 0.5, and c is a real number from 0 to 0.2.

[0355] In one exemplary embodiment of this specification, a is a real number from 0.3 to 1, b is a real number greater than 0 and less than 0.5, and c is a real number from 0 to 0.2.

[0356] In one exemplary embodiment of this specification, a is a real number from 0.3 to 0.9, b is a real number from 0.1 to 0.4, and c is a real number from 0 to 0.2.

[0357] In this specification, a, b, and c are not based on the mole fraction of the entire polymer represented by Formula 1, which contains E1 and E2, but rather on the mole fraction of the sum of A1, B1, and C1.

[0358] In one exemplary embodiment of this specification, the molar ratio of (A1+B1):(E1+E2) is 40:60 to 98:2.

[0359] An exemplary embodiment of this specification provides a polymer comprising units represented by the following chemical formula 2 and end groups represented by the following chemical formula 5.

[0360] [Chemical Formula 2]

[0361]

[0362] [Chemical Formula 5]

[0363] ＊ -[E]

[0364] In chemical formulas 2 and 5,

[0365] Ar1, Ar2, L1, and L2 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0366] R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group.

[0367] R10 to R13 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group.

[0368] n1 to n3 are each an integer from 1 to 4.

[0369] When n1 to n3 are each 2 or greater, the substituents in each bracket may be the same or different from each other.

[0370] l1 and l2 are each integers from 1 to 5.

[0371] When l1 and l2 are each 2 or larger, the substituents in each bracket may be the same or different from each other.

[0372] E is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; crosslinkable group; or combinations thereof, and

[0373] * indicates a connection point in the polymer.

[0374] In one exemplary embodiment of this specification, the polymer represented by Formula 1 may be represented by a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5. Specifically, when b and c of Formula 1 are 0, the polymer represented by Formula 1 may be represented by a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5.

[0375] In one exemplary embodiment of this specification, the polymer comprising a unit represented by chemical formula 2 and an end group represented by chemical formula 5 further comprises a unit represented by the following chemical formula 3.

[0376] [Chemical Formula 3]

[0377]

[0378] In chemical formula 3,

[0379] m is an integer of 3 or 4.

[0380] When m is 3, Z is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group.

[0381] When m is 4, Z is C; Si; or a substituted or unsubstituted tetravalent aryl group.

[0382] Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0383] Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group.

[0384] When Y is a direct bond or a substituted or unsubstituted alkylene group, Z is a substituted or unsubstituted trivalent or tetravalent aryl group, and

[0385] * indicates a connection point in the polymer.

[0386] That is, an exemplary embodiment of this specification provides a polymer comprising a unit represented by chemical formula 2, a unit represented by chemical formula 3, and an end group represented by chemical formula 5.

[0387] In this case, the polymer represented by chemical formula 1 can be represented by a polymer containing a unit represented by chemical formula 2, a unit represented by chemical formula 3, and an end group represented by chemical formula 5.

[0388] Specifically, when b in Formula 1 is a real number greater than 0 and less than 1 and c is 0, the polymer represented by Formula 1 can be represented by a polymer containing a unit represented by Formula 2, a unit represented by Formula 3, and an end group represented by Formula 5.

[0389] In one exemplary embodiment of this specification, the polymer comprising a unit represented by chemical formula 2 and an end group represented by chemical formula 5 further comprises a unit represented by the following chemical formula 4.

[0390] [Chemical Formula 4]

[0391] ＊ -[C1]- ＊

[0392] In chemical formula 4,

[0393] C1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group, and

[0394] * indicates a connection point in the polymer.

[0395] That is, an exemplary embodiment of this specification provides a polymer comprising a unit represented by chemical formula 2, a unit represented by chemical formula 4, and an end group represented by chemical formula 5.

[0396] In this case, the polymer represented by chemical formula 1 can be represented by a polymer containing a unit represented by chemical formula 2, a unit represented by chemical formula 4, and an end group represented by chemical formula 5.

[0397] Specifically, when b in chemical formula 1 is 0 and c is a real number greater than 0 and less than 1, the polymer represented by chemical formula 1 can be represented by a polymer containing a unit represented by chemical formula 2, a unit represented by chemical formula 4, and an end group represented by chemical formula 5.

[0398] Furthermore, an exemplary embodiment of this specification provides a polymer comprising a unit represented by chemical formula 2, a unit represented by chemical formula 3, a unit represented by chemical formula 4, and an end group represented by chemical formula 5.

[0399] In this case, the polymer represented by chemical formula 1 can be represented by a polymer containing units represented by chemical formula 2, units represented by chemical formula 3, units represented by chemical formula 4, and end groups represented by chemical formula 5.

[0400] Specifically, when b and c in chemical formula 1 are each real numbers greater than 0 and less than 1, the polymer represented by chemical formula 1 can be represented by a polymer containing units represented by chemical formula 2, units represented by chemical formula 3, units represented by chemical formula 4, and end groups represented by chemical formula 5.

[0401] In one exemplary embodiment of this specification, the above description of Formula 2 in Formula 1 is equivalently applied to the description of Formula 2 in a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5. For example, in a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5, Formula 2 may be represented by Formula 2-1 or Formula 2-2.

[0402] In one exemplary embodiment of this specification, when a polymer comprising a unit represented by chemical formula 2 and an end group represented by chemical formula 5 further comprises a unit represented by chemical formula 3, the above description of chemical formula 3 in chemical formula 1 is equivalent to the description of chemical formula 3. For example, in a polymer comprising a unit represented by chemical formula 2, a unit represented by chemical formula 3, and an end group represented by chemical formula 5, chemical formula 3 may be represented by any of chemical formulas 3-1 to 3-4.

[0403] The descriptions of chemical formulas 2 and 3 are even equivalent to those of polymers containing units represented by chemical formula 2, units represented by chemical formula 3, units represented by chemical formula 4, and end groups represented by chemical formula 5.

[0404] In one exemplary embodiment of this specification, when a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5 further comprises Formula 4, the definition of C1 as defined in Formula 1 is applied equivalently to the description of C1 of Formula 4. For example, in a polymer comprising a unit represented by Formula 2, a unit represented by Formula 4, and an end group represented by Formula 5, C1 of Formula 4 is any of the following structures.

[0405]

[0406] The description of C1 is even equivalent to that of polymers containing units represented by chemical formula 2, units represented by chemical formula 3, units represented by chemical formula 4, and end groups represented by chemical formula 5.

[0407] In one exemplary embodiment of this specification, in a polymer comprising a unit represented by chemical formula 2 and an end group represented by chemical formula 5, the description of E1 of chemical formula 1 is applied equivalently to E of chemical formula 5. For example, in a polymer comprising a unit represented by chemical formula 2 and an end group represented by chemical formula 5, E is the end-capping unit of the polymer.

[0408] In one exemplary embodiment of this specification, E is a crosslinkable group; or any of the following structures.

[0409]

[0410] In the structure,

[0411] R40 to R42 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; or crosslinkable group.

[0412] L40 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group.

[0413] i1 is an integer from 1 to 10.

[0414] j1 and j3 are each integers from 1 to 5.

[0415] j2 is an integer from 1 to 4.

[0416] When i1 is 2 or greater, two or more L40s are either the same or different from each other.

[0417] When j1 to j3 are each 2 or larger, the substituents in each bracket are either the same or different from each other, and

[0418] * indicates a connection point in the polymer.

[0419] The description of E applies even more equivalently to polymers containing units represented by Chemical Formula 2, units represented by Chemical Formula 3, and end groups represented by Chemical Formula 5. Furthermore, the description of E applies even more equivalently to polymers containing units represented by Chemical Formula 2, units represented by Chemical Formula 3, units represented by Chemical Formula 4, and end groups represented by Chemical Formula 5.

[0420] In one exemplary embodiment of this specification, the polymer is an alternating polymer, a block polymer, or a random polymer.

[0421] In one exemplary embodiment of this specification, Formula 1 does not imply that A1, B1, and C1 are in this order only in the polymer. Specifically, A1, B1, and C1 can be in various orders in the polymer. For example, the polymer can be in the order E1-A1-B1-C1-E2, E1-A1-C1-B1-E2, E1-B1-A1-C1-E2, E1-B1-C1-A1-E2, E1-C1-A1-B1-E2, or E1-C1-B1-A1-E2.

[0422] Furthermore, Formula 1 does not have a structure in which only A1, B1, and C1 are linked in the polymer. For example, the polymer can be linked in a variety of content ranges, such as E1-A1-B1-A1-C1-E2, E1-A1-C1-B1-C1-E2, and E1-A1-B1-C1-A1-E2. In this case, the content range of A1, B1, and C1 is determined by the equivalence ratio of the monomers used during polymer preparation.

[0423] In one exemplary embodiment of this specification, the weight-average molecular weight (Mw) of the polymer is from 25,000 g / mol to 1,000,000 g / mol. More specifically, the weight-average molecular weight (Mw) of the polymer is from 50,000 g / mol to 500,000 g / mol. More specifically, the weight-average molecular weight (Mw) of the polymer is from 50,000 g / mol to 140,000 g / mol.

[0424] When the weight-average molecular weight of the polymer meets the above range, the viscosity is suitable for exhibiting the effect of manufacturing inkjet devices and organic light-emitting devices using fine pixels.

[0425] In an exemplary embodiment of the present specification, the unit represented by Chemical Formula 2, the unit represented by Chemical Formula 3, the unit represented by Chemical Formula 4, and the terminal group represented by Chemical Formula 5 may be distributed to optimize properties of the polymer.

[0426] In an exemplary embodiment of the present specification, when the mole fraction of the unit represented by Chemical Formula 2, the mole fraction of the unit represented by Chemical Formula 3, the mole fraction of the unit represented by Chemical Formula 4, and the mole fraction of the terminal group represented by Chemical Formula 5 in the polymer are defined as a1, b1, c1 and e1, respectively, a1, b1, c1 and e1 are each real numbers satisfying 0<a1<1, 0≤b1<1, 0≤c1<1, 0<e1<1, and a1+b1+c1+e1=1.

[0427] In an exemplary embodiment of the present specification, a1 is a real number of 0.2 or greater.

[0428] In an exemplary embodiment of the present specification, a1 is a real number of 0.2 or greater and less than 1.

[0429] In an exemplary embodiment of the present specification, a1 is a real number from 0.2 to 0.9.

[0430] In an exemplary embodiment of the present specification, a1 is a real number from 0.25 to 0.85.

[0431] In an exemplary embodiment of the present specification, b1 is a real number of 0 or greater.

[0432] In an exemplary embodiment of the present specification, b1 is a real number from 0 to 0.5.

[0433] In an exemplary embodiment of the present specification, b1 is a real number greater than 0 and 0.5 or less.

[0434] In an exemplary embodiment of the present specification, b1 is a real number from 0.1 to 0.4.

[0435] In an exemplary embodiment of the present specification, c1 is a real number from 0 to 0.2.

[0436] In an exemplary embodiment of the present specification, c1 is a real number from 0 to 0.1.

[0437] In an exemplary embodiment of the present specification, c1 is 0.

[0438] In an exemplary embodiment of the present specification, e1 is a real number from 0.1 to 0.5.

[0439] In an exemplary embodiment of the present specification, e1 is a real number from 0.1 to 0.4.

[0440] In one exemplary embodiment of this specification, a1 is a real number of 0.2 or greater and less than 1, b1 is a real number from 0 to 0.5, c1 is a real number from 0 to 0.2, e1 is a real number from 0.1 to 0.5, and a1+b1+c1+e1=1.

[0441] In one exemplary embodiment of this specification, a1 is a real number of 0.2 or greater and less than 1, b1 is a real number of 0.5 or less and greater than 0, c1 is a real number of 0 to 0.2, e1 is a real number of 0.1 to 0.5, and a1+b1+c1+e1=1.

[0442] In one exemplary embodiment of this specification, a1 is a real number from 0.2 to 0.9, b1 is a real number from 0.1 to 0.4, c1 is a real number from 0 to 0.2, e1 is a real number from 0.1 to 0.5, and a1+b1+c1+e1=1.

[0443] In one exemplary embodiment of this specification, a1 is a real number from 0.25 to 0.85, b1 is a real number from 0.1 to 0.4, c1 is a real number from 0 to 0.1, e1 is a real number from 0.1 to 0.4, and a1+b1+c1+e1=1.

[0444] In one exemplary embodiment of this specification, the polymer is any of the following structures.

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475] In the above structure, a₁ is a real number satisfying 0 < a₁ < 1, b₁ is a real number satisfying 0 ≤ b₁ < 1, e₁ is a real number satisfying 0 < e₁ < 1, and a₁ + b₁ + e₁ = 1.

[0476] Specifically, in the above structure, a₁ is a real number satisfying 0 < a₁ < 1, b₁ is a real number satisfying 0 < b₁ < 1, e₁ is a real number satisfying 0 < e₁ < 1, and a₁ + b₁ + e₁ = 1.

[0477] More specifically, in the above structure, a₁ is a real number from 0.2 to 0.9, b₁ is a real number from 0.1 to 0.5, e₁ is a real number from 0.1 to 0.5, and a₁ + b₁ + e₁ = 1.

[0478] More specifically, in the structure, a1 is a real number from 0.25 to 0.85, b1 is a real number from 0.1 to 0.4, e1 is a real number from 0.1 to 0.4, and a1+b1+e1=1.

[0479] In the structure, a1, b1, and e1 are determined by the equivalent weight of the monomers added during polymer preparation.

[0480] In one exemplary embodiment of this specification, the polymer can be prepared using known polymerization techniques. For example, preparation methods such as Suzuki, Yamamoto, Stille, CN coupling reactions using metal catalysts, and arylation reactions using metal catalysts can be applied.

[0481] In one exemplary embodiment of this specification, the polymer may be deuterated. In this case, the deuterium can be replaced by applying a method using precursor materials. For example, the deuterium can be replaced by treating the non-deuterated monomer and / or polymer with a deuterated solvent in the presence of a Lewis acid H / D exchange catalyst.

[0482] In one exemplary embodiment of this specification, the molecular weight of the polymer can be controlled by adjusting the ratio of the monomers used. Furthermore, in some exemplary embodiments, the molecular weight of the polymer can be controlled by using a quenching reaction.

[0483] In one exemplary embodiment of this specification, a polymer can be used as a hole transport material. For example, the polymer can be a polymer specifically designed for transporting holes.

[0484] Furthermore, the polymer according to an exemplary embodiment of this specification can be applied to the hole transport layer of an organic light-emitting device, and thus can improve the device's performance and lifespan characteristics.

[0485] In one exemplary embodiment of this specification, the polymer can be formed into a layer using a solution method. The term 'layer' is used interchangeably with the terms 'membrane' or 'film' and refers to a coating covering a desired area. This term is not size-limited. The area can be as large as the entire device, as small as a specific functional area such as an actual visual display, or as small as a single subpixel. Layers and films can be formed using any typical deposition technique, including deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer. Continuous deposition techniques include, but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot die coating, spray coating, and continuous nozzle coating. Discontinuous deposition techniques include, but are not limited to, inkjet printing, gravure printing, and screen printing.

[0486] In one exemplary embodiment of this specification, the intrinsic viscosity of the polymer is less than 60 mL / g. This is particularly useful for inkjet printing applications, but the lower viscosity allows inkjet printing to spray more viscous liquids. Specifically, the intrinsic viscosity of the polymer is less than 50 mL / g, more specifically less than 40 mL / g, and even more specifically less than 30 mL / g.

[0487] In one exemplary embodiment of this specification, the intrinsic viscosity of the polymer is 20 mL / g or greater and less than 60 mL / g, specifically from 20 mL / g to 50 mL / g, and more specifically from 20 mL / g to 40 mL / g.

[0488] An exemplary embodiment of this specification provides a coating composition comprising the polymer described above.

[0489] In one exemplary embodiment of this specification, the coating composition further comprises a solvent. In another exemplary embodiment of this specification, the coating composition comprises a polymer and a solvent.

[0490] In one exemplary embodiment of this specification, the coating composition may be in a liquid phase. "Liquid phase" means that the composition is liquid at room temperature and atmospheric pressure.

[0491] In one exemplary embodiment of this specification, it is preferred that the solvent does not dissolve the material applied to the lower layer.

[0492] In one exemplary embodiment of this specification, when the coating composition is applied to the organic material layer of an organic light-emitting device, a solvent that does not dissolve the material in the underlying layer is used. For example, when the coating composition is applied to a hole transport layer, a solvent that does not dissolve the material in the underlying layer (first electrode, hole injection layer, etc.) is used. Therefore, it has the advantage of introducing the hole transport layer by solution method.

[0493] In one exemplary embodiment of this specification, the coating composition exhibits improved solvent resistance during heat treatment following coating.

[0494] For example, even if the coating composition is prepared by using a solvent that dissolves the polymer and the layer is manufactured by a solution method, the layer can still have resistance to the same solvent after heat treatment.

[0495] Therefore, when an organic material layer is formed by using the polymer and then subjected to a heat treatment process, a solution method can be used when applying an additional organic material layer.

[0496] In one exemplary embodiment of this specification, examples of solvents included in the coating composition include: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents, such as tetrahydrofuran and dichlorobenzene. Alkanes; aromatic hydrocarbon-based solvents, such as toluene, xylene, trimethylbenzene, and mesitylene; ketone-based solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol and their derivatives; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents, such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and solvents such as tetrahydronaphthalene, but the solvent may be used as long as it can dissolve or disperse the polymer according to one exemplary embodiment of this specification, and is not limited thereto.

[0497] In one exemplary embodiment of this specification, the solvent may be used alone or in a mixture of two or more solvents.

[0498] In one exemplary embodiment of this specification, the boiling point of the solvent is preferably 40°C to 350°C, and more preferably 80°C to 330°C, but is not limited thereto.

[0499] In one exemplary embodiment of this specification, the concentration of the polymer in the coating composition is preferably from 0.1 wt% to 20 wt% and more preferably from 0.5 wt% to 10 wt% but is not limited thereto.

[0500] An exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer comprising one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the polymer.

[0501] The organic material layer of the organic light-emitting device described in this specification may have a single-layer structure, but it may also have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports holes, and a layer that simultaneously injects and transports electrons as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it may include fewer organic layers.

[0502] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0503] In one exemplary embodiment of this specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and includes a monolayer organic material layer between the light-emitting layer and the first electrode, wherein the organic material layer comprises the polymer.

[0504] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and includes a multilayer organic material layer between the light-emitting layer and the first electrode, wherein one or more layers of the organic material layer contain the polymer.

[0505] In one exemplary embodiment of this specification, the organic material layer comprising the polymer is a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes.

[0506] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and includes one or more layers of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the first electrode, wherein one or more layers of the hole injection layer, the hole transport layer, and the electron blocking layer contain the polymer.

[0507] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and includes a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, wherein one or more of the hole injection layer and the hole transport layer contain the polymer.

[0508] In one exemplary embodiment of this specification, the organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, and a second electrode are sequentially disposed, and one or more of the hole injection layer and the hole transport layer comprise the polymer.

[0509] In one exemplary embodiment of this specification, the organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, and a second electrode are sequentially stacked, and the hole injection layer or the hole transport layer comprises the polymer.

[0510] In one exemplary embodiment of this specification, the organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, and a second electrode are sequentially stacked, and the hole transport layer comprises the polymer.

[0511] In one exemplary embodiment of this specification, an additional organic material layer may be included between the light-emitting layer and the second electrode.

[0512] In one exemplary embodiment of this specification, a single-layer organic material layer may also be included between the light-emitting layer and the second electrode.

[0513] In one exemplary embodiment of this specification, a multilayered organic material layer may be included between the light-emitting layer and the second electrode. For example, one or more layers may be included between the light-emitting layer and the second electrode, such as a hole-blocking layer, an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons.

[0514] In one exemplary embodiment of this specification, an organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and one or more of the hole injection layer and the hole transport layer comprise the polymer.

[0515] In one exemplary embodiment of this specification, an organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and the hole injection layer or the hole transport layer comprises the polymer.

[0516] In one exemplary embodiment of this specification, the organic light-emitting device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and the hole transport layer comprises the polymer.

[0517] For example, in Figure 1 The structure of an organic light-emitting device according to an exemplary embodiment of this specification is illustrated below.

[0518] Figure 1 An example is shown of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are stacked sequentially.

[0519] Figure 2 An example is shown of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron injection and transport layer 7, and a cathode 4 are stacked sequentially.

[0520] Figure 1 and Figure 2 Organic light-emitting devices are illustrated, but the structure of the organic light-emitting devices of the present invention is not limited thereto.

[0521] In one exemplary embodiment of this specification, the first electrode is an anode and the second electrode is a cathode. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

[0522] In another exemplary embodiment, the organic light-emitting device can be a conventional organic light-emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0523] In yet another exemplary embodiment, the organic light-emitting device may be an inverted organic light-emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0524] The organic light-emitting devices of the present invention can be stacked as the structures shown in the following examples.

[0525] (1) Anode / hole transport layer / light-emitting layer / cathode

[0526] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0527] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0528] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0529] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0530] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0531] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0532] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0533] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0534] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0535] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0536] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0537] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0538] (14) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0539] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0540] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0541] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0542] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer and transport layer / Cathode

[0543] In the structure described, the 'electron transport layer / electron injection layer' can be replaced by an 'electron injection and transport layer' or a 'layer that simultaneously injects and transports electrons'.

[0544] In the structure described, the 'hole injection layer / hole transport layer' can be replaced by a 'hole injection and transport layer' or a 'layer that simultaneously injects and transports holes'.

[0545] The organic light-emitting devices described in this specification can be manufactured using materials and methods known in the art, the difference being that one or more layers of organic material are manufactured to contain the polymer. Specifically, for organic light-emitting devices, one or more layers of organic material can be formed by using a coating composition containing the polymer.

[0546] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be manufactured as follows: by using physical vapor deposition (PVD) methods such as sputtering or electron beam evaporation, a metal or a conductive metal oxide, or an alloy thereof, is deposited on the substrate to form the anode; an organic material layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer is formed on the anode; and then a material that can be used as a cathode is deposited on the organic material layer. In addition to the above methods, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0547] This specification also provides a method for manufacturing organic light-emitting devices formed by using a coating composition.

[0548] Specifically, in one exemplary embodiment of this specification, the method includes: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein one or more layers of the organic material layer are formed by using a coating composition.

[0549] In one exemplary embodiment of this specification, the organic material layer formed by using the coating composition is formed by spin coating.

[0550] In another exemplary embodiment, an organic material layer formed by using a coating composition is formed by a printing method.

[0551] In yet another exemplary embodiment of this specification, examples of printing methods include, but are not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing.

[0552] The coating composition according to an exemplary embodiment of this specification is suitable for solution processing due to its structural characteristics, allowing the organic material layer to be formed by printing, and thus providing economic benefits in terms of time and cost when manufacturing devices.

[0553] In one exemplary embodiment of this specification, the formation of an organic material layer by means of a coating composition includes: coating a first electrode with the coating composition; and subjecting the coated coating composition to heat treatment or light treatment.

[0554] In another exemplary embodiment, the heat treatment time in the heat treatment of the coating composition can be within 1 hour. Specifically, the heat treatment time can be within 30 minutes.

[0555] In one exemplary embodiment of this specification, the atmosphere for heat treatment of the organic material layer formed by using the coating composition is preferably an inert gas atmosphere, such as argon or nitrogen.

[0556] When an organic material layer formed by using a coating composition is formed through a method including heat treatment or light treatment of the coating composition, solvent resistance is improved, allowing multiple layers to be formed by repeated solution deposition and crosslinking methods, and stability is improved, thereby improving the lifespan characteristics of the device.

[0557] In one exemplary embodiment of this specification, a material having a high work function is generally preferred as the anode material to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in this invention include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0558] In one exemplary embodiment of this specification, a material with a low work function is generally preferred as the cathode material to facilitate electron injection into the organic material layer. Specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, etc.

[0559] In one exemplary embodiment of this specification, the hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material used in the hole injection layer has the ability to transport holes and therefore has an excellent effect of injecting holes into the anode, anode material, light-emitting layer, and / or light-emitting material. Furthermore, the hole injection material is preferably a compound that prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and has excellent thin film formation ability. Furthermore, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0560] In one exemplary embodiment of this specification, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material used in the hole transport layer is suitably a material with high hole mobility, capable of accepting holes from the anode or hole injection layer and transferring the holes to the light-emitting layer. In one exemplary embodiment of this specification, the hole transport layer comprises the polymer.

[0561] In one exemplary embodiment of this specification, the light-emitting layer comprises an organic compound. The organic compound is a material capable of receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, to emit light in the visible light region, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxy-quinoline-aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including but not limited to azoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene, etc.

[0562] In one exemplary embodiment of this specification, the light-emitting layer may comprise a host material and a dopant material. Examples of host materials include fused aromatic ring derivatives or heterocyclic compounds. For example, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these examples. Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are fused aromatic ring derivatives substituted with substituted or unsubstituted aryl amino groups, and examples include fluorene, benzo[a]fluorene, pyrene, anthracene, etc., substituted with aryl amino groups. Diindrone pyrene, etc., and styrene amine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted aryl amine, and one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specifically, examples of styrene amine compounds include, but are not limited to, styrene amine, styrene diamine, styrene triamine, styrene tetraamine, etc. Furthermore, examples of metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0563] In one exemplary embodiment of this specification, the host material is an anthracene derivative, and the dopant material is a benzo[a]fluorene-based compound substituted with an arylamine group. Specifically, the host material is a deuterated anthracene derivative, and the dopant material is a bis(diarylamino)benzo[a]fluorene-based compound.

[0564] In one exemplary embodiment of this specification, the light-emitting layer comprises quantum dots. For example, the light-emitting layer may comprise a matrix resin and quantum dots, and those known in the art can be used as the type and amount of quantum dots.

[0565] In one exemplary embodiment of this specification, the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material used in the electron transport layer is suitably a material with high electron mobility that can readily accept electrons from the cathode and transfer them to the light-emitting layer. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0566] In one exemplary embodiment of this specification, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the cathode, and the excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation ability. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrone, copper bath (BCP) and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0567] In one exemplary embodiment of this specification, examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc.

[0568] In one exemplary embodiment of this specification, the hole blocking layer is a layer that prevents holes from reaching the cathode, and can typically be formed under the same conditions as the hole injection layer. Specifically, the hole blocking layer may use... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0569] In one exemplary embodiment of this specification, a layer adjacent to an organic material layer comprising a polymer represented by Formula 1 or a polymer comprising a unit represented by Formula 2 and an end group represented by Formula 5, such as a dam layer, comprises a compound having fluorine as a substituent.

[0570] For example, when a polymer represented by Formula 1 is contained in a hole transport layer, the dike layer adjacent to the hole transport layer (e.g., one or more of a hole injection layer and a light-emitting layer) contains fluorine.

[0571] When a layer adjacent to an organic material layer containing a polymer represented by Formula 1 or a polymer containing a unit represented by Formula 2 and an end group represented by Formula 5 contains fluorine, it has the effect of forming a uniform layer because the dipole moment changes according to the fluorine.

[0572] Depending on the material to be used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-emitting type.

[0573] Invention Embodiments

[0574] In the following description, this specification will be described in detail with reference to embodiments used to specifically describe this specification. However, the embodiments according to this specification can be modified in various ways and should not be construed as limiting the scope of this application to the embodiments described in detail below. Embodiments of this application are provided to explain this specification more completely to those skilled in the art.

[0575] <Synthesis example>

[0576] Synthesis Example 1. Preparation of Polymer 1

[0577]

[0578] (1) Preparation of compound A-1

[0579] Compound q-1 (50.0 g, 1.00 equivalent), compound q-2 (65.2 g, 1.35 equivalent), potassium carbonate (K₂CO₃) (78.7 g, 2.5 equivalent), and bis(tri-tert-butylphosphine)palladium(0) (1.74 g, 0.015 equivalent) were introduced into a round-bottom flask equipped with a condenser. Tetrahydrofuran (THF) (500 mL) and distilled water (300 mL) were then separately added to the flask, and the flask was heated to 60 °C and stirred for 6 hours. After terminating the reaction by adding distilled water to the flask, the organic solvent was extracted and concentrated under reduced pressure to prepare compound A-1 (50.1 g) in liquid form.

[0580] (2) Preparation of compound B-1

[0581] In a round-bottom flask equipped with a condenser, compound A-2 (41.0 g, 1.00 equivalent) and the previously prepared compound A-1 (50.0 g, 3.0 equivalent) were dissolved in xylene (200 mL). When the solution was completely dissolved, sodium tert-butoxide (40.0 g, 5.00 equivalent) and bis(tri-tert-butylphosphine)palladium(0) (2.1 g, 0.05 equivalent) were added, and the resulting mixture was refluxed at 120 °C for 3 hours. After terminating the reaction by injecting distilled water into the flask, the organic solvent was extracted with ethyl acetate and distilled water, and the mixture was precipitated with toluene and hexane to prepare compound B-1 as a white solid.

[0582] (3) Preparation of compound C-1

[0583] In a round-bottom flask equipped with a condenser, the previously prepared compound B-1 (15.1 g, 1.00 equivalent), 4-bromo-4'-iodo-1,1'-biphenyl (13.16 g, 2.50 equivalent), and sodium tert-butoxide (7.0 g, 5.00 equivalent) were dissolved in toluene (200 mL). When the solution was completely dissolved, tris(dibenzylacetone)dipalladium(0) (0.67 g, 0.05 equivalent) and 1,1'-bis(diphenylphosphine)ferrocene (0.81 g, 0.10 equivalent) were introduced into the flask, and the resulting mixture was refluxed at 90 °C for 8 hours. After terminating the reaction by injecting distilled water into the flask, the organic solvent was extracted with ethyl acetate and distilled water, and compound C-1 with a purity of 99.7% was prepared by column chromatography.

[0584] (4) Preparation of compound D-1

[0585] In a round-bottom flask equipped with a condenser, 10.00 g (1.00 equivalent) of the previously prepared C-1, 14 g (2.00 equivalent) of bis(pinacol)diboron, and 1.60 g (3.00 equivalent) of potassium tert-butoxide were dissolved in 200 mL of toluene. When the solution was completely dissolved, 0.20 g (0.04 equivalent) of [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) chloride (Pd(dppf)) was introduced into the flask, and the resulting mixture was refluxed at 90 °C for 8 hours. After terminating the reaction with deionized water, the organic solvent was extracted with ethyl acetate and distilled water, and compound D-1 with a purity of 99.3% was prepared by column chromatography.

[0586] (5) Preparation of polymer 1

[0587]

[0588] Compound D-1 (0.765 mmol), 4,4”-dibromo-5'-(4-bromophenyl)-1,1':3',1”-terphenyl (0.158 mmol) and 4-bromo-4'-propyl-1,1'-biphenyl (0.369 mmol) were placed in a round-bottom flask and dissolved in toluene (11 mL) to prepare the first solution.

[0589] Bis(1,5-cyclooctadiene)nickel (0) (2.42 mmol) was introduced into a 50 mL Schlenk tube. 2,2'-Bipyridine (2.42 mmol) and 1,5-cyclooctadiene (2.42 mmol) were placed in a scintillation flask and then dissolved in N,N'-dimethylformamide (5.5 mL) and toluene (11 mL) to prepare a second solution.

[0590] The second solution was placed in a Schlenk tube and stirred at 50°C for 30 minutes. The first solution was then added to the Schlenk tube, and the resulting solution was stirred at 50°C for 3 hours. After terminating the reaction by slowly adding HCl and methanol (methanol:HCl = 95:5 (volume:volume)), the resulting solution was stirred for 45 minutes, and the resulting solid was filtered. The dried solid was dissolved in toluene (1% by weight / volume) and purified by passing it through a column containing silica gel and basic alumina (6 g each). Polymer 1 was prepared by grinding the toluene solution obtained with acetone.

[0591] Synthesis Example 2. Preparation of Polymer 2

[0592]

[0593] Polymer 2 was prepared in the same manner as in Synthesis Example 1, except that 3,3”-dibromo-5'-(3-bromophenyl)-1,1':3',1”-terphenyl was used instead of 4,4”-dibromo-5'-(4-bromophenyl)-1,1':3',1”-terphenyl in (5) of Synthesis Example 1.

[0594] Synthesis Example 3. Preparation of Polymer 3

[0595]

[0596] Polymer 3 was prepared in the same manner as in Synthesis Example 1, except that 1,3,5-tribromobenzene was used instead of 4,4”-dibromo-5'-(4-bromophenyl)-1,1':3',1”-terphenyl in (5) of Synthesis Example 1.

[0597] Synthesis Example 4. Preparation of Polymer 4

[0598]

[0599] Polymer 4 was prepared in the same manner as in Synthesis Example 1, except that tris(4-bromophenyl)(phenyl)silane was used instead of 4,4”-dibromo-5'-(4-bromophenyl)-1,1':3',1”-terphenyl in (5) of Synthesis Example 1.

[0600] Synthesis Example 5. Preparation of Polymer 5

[0601]

[0602] Polymer 5 was prepared in the same manner as in Synthesis Example 1, except that tetra(4-bromophenyl)silane was used instead of 4,4”-dibromo-5'-(4-bromophenyl)-1,1':3',1”-terphenyl in (5) of Synthesis Example 1.

[0603] Synthesis Example 6. Preparation of Polymer 6

[0604]

[0605] Polymer 6 was prepared in the same manner as in Synthesis Example 1, except that compound D-2 was used instead of compound D-1 in (5) of Synthesis Example 1.

[0606] Synthesis Example 7. Preparation of Polymer 7

[0607]

[0608] Polymer 7 was prepared in the same manner as in Synthesis Example 2, except that compound D-2 was used instead of compound D-1 in Synthesis Example 2.

[0609] Synthesis Example 8. Preparation of Polymer 8

[0610]

[0611] Polymer 8 was prepared in the same manner as in Synthesis Example 3, except that compound D-2 was used instead of compound D-1 in Synthesis Example 3.

[0612] Synthesis Example 9. Preparation of Polymer 9

[0613]

[0614] Polymer 9 was prepared in the same manner as in Synthesis Example 4, except that compound D-2 was used instead of compound D-1 in Synthesis Example 4.

[0615] Synthesis Example 10. Preparation of Polymer 10

[0616]

[0617] Polymer 10 was prepared in the same manner as in Synthesis Example 5, except that compound D-2 was used instead of compound D-1 in Synthesis Example 5.

[0618] <Experimental Example 1> Measurement of Molecular Weight

[0619] Experimental Example 1-1.

[0620] The number-average molecular weight (Mn), weight-average molecular weight (Mw), and polydispersity index (PDI) of polymer 1 prepared in Synthesis Example 1 were measured using a GPC (manufactured by Agilent, PLgel HFIPGEL column).

[0621] The polydispersity index is calculated using the following equation (1).

[0622] Equation (1): PDI = weight-average molecular weight (Mw) / number-average molecular weight (Mn)

[0623] Experimental Examples 1-2 to 1-10.

[0624] The number-average molecular weight (Mn), weight-average molecular weight (Mw), and polydispersity index (PDI) were measured in the same manner as in Experimental Example 1-1, except that polymers in Table 1 below were used instead of polymer 1 in Experimental Example 1-1.

[0625] Comparative Example 1-1.

[0626] The number-average molecular weight (Mn), weight-average molecular weight (Mw), and polydispersity index (PDI) were measured in the same manner as in Experimental Example 1-1, except that polymer Q was used instead of polymer 1 in Experimental Example 1-1.

[0627] The structure of polymer Q used in Comparative Example 1-1 is as follows.

[0628]

[0629] The GPC results measured in Experimental Examples 1-1 to 1-10 and Comparative Example 1-1 are shown in Table 1 below.

[0630] [Table 1]

[0631]

[0632] Experimental Example 2. Fabrication of Organic Light-Emitting Devices

[0633] Experimental Example 2-1.

[0634] (1) Materials

[0635] As a dopant, a compound based on bis(diarylamino)benzo[a]fluorene as described in US8,465,848B2 was used.

[0636] As the HIL, the material described in US 7,351,358B2 is used. Specifically, a hole injection material prepared from an aqueous dispersion of a conductive polymer and a polymerizable fluorinated sulfonic acid is used.

[0637] As the main component, deuterated anthracene compounds as described in WO2011-028216A1 are used.

[0638] (2) Manufacturing of the device

[0639] A thin coating with a thickness of An indium tin oxide (ITO) glass substrate was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, the substrate was ultrasonically washed with isopropanol and acetone solvents, dried, then rinsed for 5 minutes, and then dried again.

[0640] Prior to device fabrication, the washed and patterned ITO was treated with UV ozone for 10 minutes. After ozone treatment, an aqueous dispersion of HIL was spin-coated onto the ITO surface, and the solvent was removed by heat treatment to form a hole injection layer with a thickness of approximately 40 nm. A toluene solution containing 1.5 wt% of polymer 1 prepared in Synthesis Example 1 was spin-coated onto the hole injection layer, and the solvent was removed by heat treatment to form a hole transport layer with a thickness of approximately 100 nm. A methyl benzoate solution containing a host and dopant (host:dopant = 93:7 (wt%)) at a concentration of 2.0 wt% was spin-coated onto the hole transport layer to form a light-emitting layer with a thickness of approximately 100 nm. Subsequently, the ITO was transported to a vacuum deposition apparatus, and a BCP was vacuum-deposited on the light-emitting layer to a thickness of 35 nm to form an electron injection and transport layer. LiF and aluminum were sequentially deposited on the electron injection and transport layers to thicknesses of 1 nm and 100 nm, respectively, to form a cathode.

[0641] During the aforementioned process, the deposition rates of lithium fluoride and aluminum at the cathode are maintained at [specific values ​​to be filled in]. and And the vacuum level during deposition was maintained at 2×10⁻⁶. -7 Up to 5×10 -6 Entrust.

[0642] Experimental Examples 2-2 to 2-10.

[0643] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that polymers listed in Table 2 below were used instead of polymer 1 in Experimental Example 2-1.

[0644] Comparative Example 2-1.

[0645] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that polymers listed in Table 2 below were used instead of polymer 1 in Experimental Example 2-1.

[0646] At 10mA / cm 2 The results of measuring the performance of the organic light-emitting devices fabricated in Experimental Examples 2-1 to 2-10 and Comparative Example 2-1 at a current density are shown in Table 2 below.

[0647] In Table 2 below, the external quantum efficiency is determined by (number of emitted photons) / (number of injected charge carriers), and the following color coordinates are the x and y coordinates according to the CIE chromaticity diagram (Commission internationale de l'Eclairage, 1931), CE / CIEy is the value obtained by dividing the luminous efficiency (cd / A) by the color coordinate (y) value.

[0648] [Table 2]

[0649]

[0650] As shown in Table 2, it can be determined that, compared with organic light-emitting devices using polymers containing linear alkyl groups (Comparative Example 2-1), organic light-emitting devices using polymers containing branched alkyl groups according to this specification (Experimental Examples 2-1 to 2-10) have lower driving voltages and improved efficiency.

[0651] Experimental Example 3. Measurement of Service Life and Drive Stability

[0652] The organic light-emitting devices fabricated in Experimental Example 2-1 and Comparative Example 2-1 were stored at 1000 nits and room temperature, and their stability was measured.

[0653] It was determined that when comparing the time (T95) it takes for the brightness to decrease from the initial brightness to 95%, the time taken for the organic light-emitting device manufactured in Experimental Example 2-1 was more than twice that taken for the organic light-emitting device manufactured in Comparative Example 2-1. This means that it takes longer to reduce the brightness in Experimental Example 2-1 than in Comparative Example 2-1, and thus it can be determined that the organic light-emitting device manufactured in Experimental Example 2-1 has better long-term stability (lifespan) than the organic light-emitting device in Comparative Example 2-1.

[0654] Furthermore, based on the results of measuring the progressive driving voltage of the organic light-emitting device manufactured in Experimental Example 2-1 and the organic light-emitting device manufactured in Comparative Example 2-1, it can be determined that in the device of Comparative Example 2-1, the magnitude of the injected voltage to generate light identical to the initial light increases over time, while in the device of Experimental Example 2-1, a constant amount of light is achieved even when a low voltage is injected as at the beginning. Specifically, it can be confirmed that in the case of the device manufactured in Comparative Example 2-1, light identical to the initial light is generated only when a voltage of 0.2V or higher is injected over time, while in the case of the device manufactured in Experimental Example 2-1, light identical to the initial light is generated even when a voltage below 0.1V is injected at the same time as when 0.2V or higher is injected in Comparative Example 2-1. That is, it can be determined that the progressive driving voltage stability of the organic light-emitting device manufactured in Experimental Example 2-1 is improved compared to that of the organic light-emitting device manufactured in Comparative Example 2-1.

[0655] With a progressive driving voltage, stability is improved due to the formation of a uniform thin film. Furthermore, based on the above experimental results, the polymer used in Experimental Example 2-1 has improved solubility compared to the polymer used in Comparative Example 2-1, thereby forming a uniform thin film, which makes it possible to predict that the progressive driving voltage will exhibit stability.

[0656] Although a preferred exemplary embodiment of the present invention (hole transport layer) has been described above, the present invention is not limited thereto, and various modifications can be made and implemented within the scope of the claims and the detailed description of the present invention, and such modifications also fall within the scope of the present invention.

Claims

1. A polymer represented by the following chemical formula 1: [Chemical Formula 1] in, In Chemical Formula 1, A1 is represented by the following Chemical Formula 2, B1 is represented by the following Chemical Formula 3, C1 is a substituted or unsubstituted arylene; or a substituted or unsubstituted divalent heterocyclic group, and E1 and E2 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamino group; a substituted or unsubstituted siloxanyl group; a crosslinkable group; or a combination thereof, a, b and c are each molar fractions, a is a real number satisfying 0 < a ≤ 1, b is a real number satisfying 0 ≤ b < 1, c is a real number satisfying 0 ≤ c < 1, a+b+c=1, [Chemical Formula 2] In Chemical Formula 2, Ar1, Ar2, L1 and L2 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene, R1 to R3 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxanyl group, R10 to R13 are the same as or different from each other, and each is independently an alkyl group having 1 to 10 carbon atoms, n1 to n3 are each an integer of 1 to 4, when n1 to n3 are each 2 or greater, the substituents in each parenthesis are the same as or different from each other, l1 and l2 are each an integer of 1 to 5, when l1 and l2 are each 2 or greater, the structures in each parenthesis are the same as or different from each other, * represents a connection site in the polymer, [Chemical Formula 3] In Chemical Formula 3, m is an integer of 3 or 4, when m is 3, Z is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group, when m is 4, Z is C; Si; or a substituted or unsubstituted tetravalent aryl group, Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group, when Y is a direct bond or a substituted or unsubstituted alkylene, Z is a substituted or unsubstituted trivalent or tetravalent aryl group, and * represents a connection site in the polymer.

2. The polymer according to claim 1, wherein E1 and E2 are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a crosslinkable group; or a combination thereof.

3. The polymer according to claim 1, wherein E1 and E2 are the same as or different from each other, and each is independently a crosslinkable group; or any one of the following structures: In said structures, R40 to R42 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable group, L40 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group. i1 is an integer from 1 to 10. j1 and j3 are each integers from 1 to 5. j2 is an integer from 1 to 4. When i1 is 2 or greater, two or more L40s are either the same or different from each other. When j1 to j3 are each 2 or larger, the substituents in each bracket are either the same or different from each other, and * indicates a connection point in the polymer.

4. A polymer comprising: a unit represented by the following chemical formula 2; and The end group represented by the following chemical formula 5: [Chemical Formula 2] [Chemical Formula 5] in, In chemical formulas 2 and 5, Ar1, Ar2, L1, and L2 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group. R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group. R10 to R13 may be the same as or different from each other, and each is independently an alkyl group having 1 to 10 carbon atoms. n1 to n3 are each an integer from 1 to 4. When n1 to n3 are each 2 or greater, the substituents in each bracket may be the same or different from each other. l1 and l2 are each integers from 1 to 5. When l1 and l2 are each 2 or larger, the structures within each set of parentheses may be the same or different from each other. E is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylamino; substituted or unsubstituted siloxane; crosslinkable group; or combinations thereof, and * indicates a connection point in the polymer.

5. The polymer according to claim 4, further comprising a unit represented by the following chemical formula 3: [Chemical Formula 3] in, In chemical formula 3, m is an integer of 3 or 4. When m is 3, Z is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group. When m is 4, Z is C; Si; or a substituted or unsubstituted tetravalent aryl group. Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group. When Y is a direct bond or a substituted or unsubstituted alkylene group, Z is a substituted or unsubstituted trivalent or tetravalent aryl group, and * indicates a connection point in the polymer.

6. The polymer according to claim 4, further comprising a unit represented by the following chemical formula 4: [Chemical Formula 4] in, In chemical formula 4, C1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group, and * indicates a connection point in the polymer.

7. The polymer according to claim 4, wherein E is a crosslinkable group; or any of the following structures: In the structure, R40 to R42 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; or crosslinkable group. L40 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted aryl group. i1 is an integer from 1 to 10. j1 and j3 are each integers from 1 to 5. j2 is an integer from 1 to 4. When i1 is 2 or greater, two or more L40s are either the same or different from each other. When j1 to j3 are each 2 or larger, the substituents in each bracket are either the same or different from each other, and * indicates a connection point in the polymer.

8. The polymer according to any one of claims 1 to 7, wherein chemical formula 2 is the following chemical formula 2-1: [Chemical Formula 2-1] In chemical formula 2-1, R1 to R3, R10 to R13, Ar1, Ar2, and n1 to n3 are the same as those defined in Chemical Formula 2. L3 and L4 may be identical or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group. R15 and R16 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamino group; or a substituted or unsubstituted siloxane group. n15 and n16 are each integers from 1 to 4. When n15 and n16 are each 2 or greater, the substituents in each bracket may be the same or different from each other. l3 and l4 are each integers from 1 to 4. When l3 and l4 are each 2 or larger, the structures within each bracket may be the same or different from each other, and * indicates a connection point in the polymer.

9. The polymer according to any one of claims 1, 2, 3 and 5, wherein chemical formula 3 is represented by any one of the following chemical formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In chemical formulas 3-1 to 3-4, Z1 is CRa; SiRa; N; or a substituted or unsubstituted trivalent aryl group. Z2 and Z3 may be identical or different from each other, and each is independently C; Si; or a substituted or unsubstituted tetravalent aryl group. L10 is a direct bond; or a substituted or unsubstituted aryl group. Ra represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. R20 to R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; alkoxy; aryloxy; fluoroalkoxy; siloxane; substituted or unsubstituted amino group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or crosslinkable group, and adjacent groups may be bonded to each other to form a ring. k1 is an integer from 1 to 4. k2 is an integer from 1 to 5. When k1 is 2 or greater, the substituents in parentheses may be the same or different from each other. When k2 is 2 or greater, the substituents in parentheses are the same as or different from each other, and * is the connection point in the polymer.

10. The polymer according to any one of claims 1 to 7, wherein the polymer is any one of the following structures: In said structure, a1 is a real number satisfying 0<a1<1, b1 is a real number satisfying 0≤b1<1, e1 is a real number satisfying 0<e1<1, and a1+b1+e1=1.

11. An organic light-emitting device, comprising: a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode, the organic material layer having one or more layers, wherein one or more layers of the organic material layer comprise the polymer according to any one of claims 1 to 7.

12. The organic light-emitting device according to claim 11, wherein the organic material layer containing the polymer is a hole injection layer, a hole transport layer, or a layer that both injects and transports holes.

Images