Polycyclic compound and organic electroluminescent device containing same

Abstract

A polycyclic compound represented by formula (1) provides a highly efficient and long-life organic electroluminescent element, wherein at least one of Cy1 and Cy2 has a chemical structure represented by general formula (A1) or (B1). In general formulae (1), (A1), and (B1), R1 to R31, Cy1 to Cy2, L1, L2, and X1 to X3 are completely the same as defined in the description. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a polycyclic compound, a material for an organic electroluminescent device containing the compound, and an organic electroluminescent device containing the compound. Background Art

[0002] Organic electroluminescent devices include an anode, a cathode, and a plurality of organic layers disposed between the anode and the cathode. Since blue light has a short wavelength and high energy, it is very important to develop efficient blue light materials to improve device performance.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Korean Publication No. KR2022113279A

[0006] Patent Document 2: International Publication No. WO2021107681A1

[0007] Patent document 3: China Publication No. CN116478194A

[0008] Patent Document 4: International Publication No. WO2021107743A1

[0009] Patent Document 5: Korean Publication No. KR2023134996A

[0010] Patent Document 6: International Publication No. WO2023096399A1

[0011] Patent document 7: European publication No. EP4056576A1

[0012] Patent Document 8: Korean Publication No. KR2017126081A

[0013] Patent document 9: China Publication No. CN118475566A Summary of the invention

[0014] Problems to be solved by the present invention

[0015] The blue light materials developed in the past have the disadvantages of low efficiency and short lifespan, and there is an urgent need to develop a high-performance blue light material.

[0016] Means used to solve problems

[0017] The present inventors have found that the compound of the following formula (1) has the function of improving the efficiency and life of a device.

[0018] In one embodiment, a compound of the general formula (1) (hereinafter sometimes also referred to as compound (1)) is provided.

[0019] [Chemistry 1]

[0020]

[0021] In formula (1),

[0022] L1 is a single bond or L11, L11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0023] L2 is a single bond or L22, L22 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0024] X1 is an oxygen atom, a sulfur atom, or a selenium atom;

[0025] R1 to R4, R5 to R7 and R8 to R11 each independently represent a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0026] Wherein, two adjacent ones of R1 to R4, R5 to R7 and R8 to R11 independently represent hydrogen atoms, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure;

[0027] Cy1 to Cy2 are the same or different from each other, and at least one of Cy1 to Cy2 is the following formula (A1) or (B1),

[0028] [Chemistry 2]

[0029]

[0030] In the above formulas (A1) and (B1),

[0031] One of R12 to R21 and R22 to R31 is a single bond bonded to the above formula (1);

[0032] R12 to R21 and R22 to R31 which are not single bonds to the above formula (1) are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0033] Among them, two adjacent ones of R12 to R21 and R22 to R31 that are not single bonds to the above formula (1) each independently represent a hydrogen atom, deuterium, or the above substituent, or are bonded to each other to form a ring structure;

[0034] X2 to X3 are oxygen atoms or sulfur atoms.

[0035] In another embodiment, the present invention provides a material for an organic electroluminescent device comprising compound (1).

[0036] In another embodiment, the present invention provides an organic light-emitting device, which is an organic electroluminescent device having a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer contains compound (1) as a fluorescent dopant and at least one host material.

[0037] Effects of the Invention

[0038] The polycyclic compound (1) has the function of improving the blue light emitting efficiency and improving the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 It is a schematic diagram of a device comprising the polycyclic compound (1) of the present invention. DETAILED DESCRIPTION

[0040] The following specific implementation schemes are used to further illustrate the effects of the technical solutions of the present invention. It should be noted that the following specific implementation schemes are intended to illustrate the technical advantages of the present invention and are not intended to limit the scope of the present application.

[0041] The description of "substituted or unsubstituted carbon atoms" in the specification refers to the number of carbon atoms when not substituted. The description of "substituted or unsubstituted atoms" refers to the number of atoms when not substituted. The description of "ring carbon atoms" refers to the number of carbon atoms in the atoms of the compound itself that constitute the cyclic structure. The description of "cyclic compound" or "cyclic structure" refers to a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound, and the carbon atoms on the substituents in the above cyclic structures are not counted in the number of ring carbon atoms. "Heavy hydrogen" in this specification uniformly refers to hydrogen isotopes with different numbers of neutrons, which can be protium, deuterium, or tritium.

[0042] The polycyclic compound (1) according to one embodiment of the present specification is represented by the general formula (1).

[0043] [Chemistry 3]

[0044]

[0045] In formula (1),

[0046] L1 is a single bond or L11, L11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0047] L2 is a single bond or L22, L22 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0048] X1 is an oxygen atom, a sulfur atom, or a selenium atom;

[0049] R1 to R4, R5 to R7 and R8 to R11 each independently represent a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0050] Wherein, two adjacent ones of R1 to R4, R5 to R7 and R8 to R11 independently represent hydrogen atoms, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure;

[0051] Cy1 to Cy2 are the same or different from each other, and at least one of Cy1 to Cy2 is the following formula (A1) or (B1),

[0052] [Chemistry 4]

[0053]

[0054] In the above formulas (A1) and (B1),

[0055] One of R12 to R21 and R22 to R31 is a single bond bonded to the above formula (1);

[0056] R12 to R21 and R22 to R31 which are not single bonds to the above formula (1) are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0057] Among them, two adjacent ones of R12 to R21 and R22 to R31 that are not single bonds to the above formula (1) each independently represent a hydrogen atom, deuterium, or the above substituent, or are bonded to each other to form a ring structure;

[0058] X2 to X3 are oxygen atoms or sulfur atoms.

[0059] In one embodiment of the present invention, when two adjacent substituents R9 and R10 do not form a ring structure, the compound (1) is represented by the following formula (2):

[0060] [Chemistry 5]

[0061]

[0062] In formula (2),

[0063] R32 and R33 are independently substituted or unsubstituted aryl having 6 to 30 ring carbon atoms and substituted or unsubstituted heteroaryl having 5 to 30 ring atoms;

[0064] R1 to R4, R5 to R7, R8 to R9, R11, X1, L1 to L2 and Cy1 to Cy2 are as defined in formula (1).

[0065] In another embodiment of the present invention, two adjacent substituents R9 and R10 are bonded to each other to form a ring structure, and the compound (1) is represented by the following formula (3):

[0066] [Chemistry 6]

[0067]

[0068] In formula (3),

[0069] Cy3 is represented by any of the following formulas (C1), (D1) or (E1),

[0070] [Chemistry 7]

[0071]

[0072] In formula (D1), R34 to R37 are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0073] Among them, two adjacent ones of R34 to R37 each independently represent a hydrogen atom, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure.

[0074] Hereinafter, each symbol in Formulas (1) to (3) and (A1) to (E1) and the following Formulas (4) to (16) and (F1) will be described in detail.

[0075] L1 is a single bond or L11, L11 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring carbon atoms; in one embodiment of the present invention, L1 is a bonded single bond, and in another embodiment, L1 is L11.

[0076] In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L11, the arylene group having 6 to 30 ring carbon atoms is selected from the group consisting of phenylene, biphenylene and naphthylene.

[0077] L2 is a single bond or L22, L22 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring carbon atoms; in one embodiment of the present invention, L2 is a bonded single bond, and in another embodiment, L2 is L22.

[0078] In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L22, the arylene group having 6 to 30 ring carbon atoms is selected from the group consisting of phenylene, biphenylene and naphthylene groups.

[0079] Wherein, L1 and L2 are the same as or different from each other and are independently selected from the above-mentioned arylene groups or bonded single bonds.

[0080] X1 is an oxygen atom, a sulfur atom, or a selenium atom. In one embodiment of the present invention, X1 is an oxygen atom, and in another embodiment of the present invention, X2 is a sulfur atom.

[0081] R1-R4, R5-R7 and R8-R11 are independently hydrogen atoms, deuterium atoms or substituents selected from halogen atoms, cyano groups, nitro groups, substituted or unsubstituted alkyl groups having 1-30 carbon atoms, preferably 1-8 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-30 ring carbon atoms, preferably 3-8 ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 ring carbon atoms, preferably 6-18 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7-36 carbon atoms, preferably 7-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-30 ring carbon atoms, preferably 3-8 ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 ring carbon atoms, preferably 6-18 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7-36 carbon atoms, preferably 7-20 ring carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-30 ring carbon atoms, preferably 3-3 ... The group consisting of a substituted heteroaryl group having 5 to 30, preferably 5 to 24, ring-forming atoms; a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24 ring atoms; and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 8, ring-forming carbon atoms and a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18.

[0082] Among them, two adjacent groups selected from R1 to R4, R5 to R7 and R8 to R11 each independently represent a hydrogen atom, a deuterium atom, or the above-mentioned substituents, or are bonded to each other to form a ring structure. That is, the two adjacent groups do not form a ring structure but are each independently represented by a hydrogen atom, a deuterium atom or the above-mentioned substituents, or the two adjacent groups are bonded to each other to form a ring structure.

[0083] That is, R1 to R4, R5 to R7 and R8 to R11 each independently represent a hydrogen atom, a deuterated hydrogen atom or a substituent, or are bonded to an adjacent group selected from R1 to R4, R5 to R7 and R8 to R11 to form a ring structure.

[0084] The ring structure may include, but is not limited to, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted aromatic heterocycle having 5 to 18 ring atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, or a substituted or unsubstituted aliphatic heterocycle having 5 to 18 ring atoms.

[0085] The aromatic hydrocarbon ring having 6 to 18 ring carbon atoms may include, but is not limited to, a naphthalene ring, a pyrene ring, an anthracene ring, a biphenylene ring, a benzanthracene ring, a triphenylene ring, a phenanthrene ring, a triphenylene ring, or a benzene ring, and a phenanthrene ring or a benzene ring is particularly preferred.

[0086] The aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms may include, but is not limited to, a cyclohexadiene ring, a cyclopentadiene ring, a cyclopentene ring, a cyclohexene ring, or an aliphatic ring obtained by partially hydrogenating the above aromatic hydrocarbon rings.

[0087] The aromatic heterocycle having 5 to 18 ring atoms may include, but is not limited to, a benzocarbazole ring, a pyridine ring, an isobenzofuran ring, a pyrazole ring, a furan ring, a benzimidazole ring, a dibenzofuran ring, a dibenzothiophene ring, a thiophene ring, an isoindole ring, a naphthobenzofuran ring, a carbazole ring, a benzothiophene ring, a pyrrole ring, an imidazole ring, an indole ring, a benzofuran ring, or an indole ring.

[0088] The aliphatic ring having 5 to 18 ring atoms can be obtained by partially hydrogenating the aromatic heterocycle having 5 to 18 ring atoms.

[0089] The halogen atom mentioned above may be one or more of fluorine, chlorine, bromine and iodine, preferably a fluorine atom.

[0090] The above-mentioned substituted or unsubstituted alkyl group having 1 to 30 carbon atoms includes, but is not limited to, heptyl, methyl, sec-butyl, ethyl, pentyl, nonyl, isobutyl, undecyl, tert-butyl, hexyl, octyl, n-propyl, decyl, n-butyl or dodecyl, and in a specific embodiment, methyl or tert-butyl is preferred.

[0091] The above-mentioned substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms includes, but is not limited to, cyclobutyl, cyclopropyl, cyclopentyl, cycloheptyl, or cyclohexyl. In a specific embodiment, cyclopentyl or cyclohexyl is preferred.

[0092] The above-mentioned substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms includes, but is not limited to, triphenylene, phenanthene, terphenylene, fluorenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, triphenylene, biphenylene, pyrene, fluoranthenyl, benzanthryl, diphenylene, perylenyl, or phenyl. In a specific embodiment, phenyl, biphenylene, terphenylene, or naphthyl is preferred.

[0093] The substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms includes, but is not limited to, benzyl, phenethyl or phenylpropyl. In a specific embodiment, benzyl is preferred.

[0094] The substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms may be exemplified, but not limited to, naphthobenzothiophenyl, pyridyl, pyrazinyl, imidazopyridyl, benzoxazolyl, carbazolyl, isothiazolyl, oxadiazolyl, benzofuranyl, oxazolyl, benzisothiazolyl, pyrazolyl, isoindolyl, furanyl, isoquinolyl, quinolizinyl, indazolyl, phenoxazinyl, quinoxalinyl, phenolazinyl, acridinyl, phenazinyl, naphthobenzofuranyl, benzothiophenyl, isobenzo Furanyl, cinnolinyl, isoxazolyl, thienyl, phenanthrolinyl, isobenzothienyl, benzimidazolyl, triazinyl, benzisoxazolyl, thiazolyl, indolizinyl, triazolyl, xanthenyl, pyrrolyl, pyridazinyl, imidazolyl, thiadiazolyl, indolyl, quinolinyl, quinazolinyl, benzothiazolyl, phenanthridinyl, phenothiazinyl, dibenzofuranyl, dibenzothienyl, or tetrazolyl, as long as the heteroatom type is an oxygen atom, a nitrogen atom or a sulfur atom, and the number of heteroatoms is 1 to 5.

[0095] In the above-mentioned disubstituted amino group of the substituent selected from substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, the aryl sites having 6 to 30 ring carbon atoms include, but are not limited to, triphenylene, phenanthene, terphenyl, fluorenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, triphenylene, biphenyl, pyrenyl, fluoranthene, benzanthryl, biphenylene, perylene, or phenyl, and the heteroaryl sites having 5 to 30 ring atoms include, but are not limited to, dibenzothiophenyl, imidazolyl, triazolyl, thienyl, pyrazinyl, isoxazolyl, cinnolinyl, oxadiazole ... oxazolyl, benzimidazolyl, quinazolinyl, thiazolyl, furanyl, phenanthrolinyl, isobenzofuranyl, isobenzothiophenyl, xanthenyl, indolyl, phenanthridinyl, benzothiazolyl, indolizinyl, benzisoxazolyl, phenothiazinyl, quinolinyl, dibenzofuranyl, pyridinyl, acridinyl, indazolyl, thiadiazolyl, naphthobenzothiophenyl, carbazolyl, isothiazolyl, phenoxazinyl, imidazopyridinyl, benzofuranyl, pyrrolyl, isoindolyl, pyrazolyl, phenazinyl, benzisothiazolyl, benzoxazolyl, naphthobenzofuranyl, benzothiophenyl, pyridazinyl, triazinyl, oxazolyl, tetrazolyl, quinolizinyl, isoquinolinyl, phenazinyl, or quinoxalinyl.

[0096] In the above-mentioned monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms and a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, the alkyl group with 1 to 30 carbon atoms includes, but is not limited to, heptyl, methyl, sec-butyl, ethyl, pentyl, nonyl, isobutyl, undecyl, tert-butyl, hexyl, octyl, n-propyl, decyl, n-butyl or dodecyl, and in a specific embodiment, methyl or tert-butyl is preferred, and the aryl group with 6 to 30 ring carbon atoms includes, but is not limited to, triphenylene, phenanthene, terphenylene, fluorenyl, naphthyl, anthracenyl, phenanthrenyl, phenanthrenyl, biphenylene, pyrenyl, fluoranthenyl, benzanthryl, biphenylene, perylene, or phenyl. In one embodiment of the present invention, the silyl group is preferably triphenylsilane.

[0097] One of R12 to R21 and R22 to R31 is a single bond bonding to the above formula (1).

[0098] R12 to R21 and R22 to R31 which are not single bonds to formula (1) are independently hydrogen atoms, deuterium atoms, or substituents selected from halogen atoms; cyano groups; nitro groups; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, preferably 1 to 8 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 30 ring carbon atoms, preferably 3 to 8 ring carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms; substituted or unsubstituted aralkyl groups having 7 to 36 carbon atoms, preferably 7 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24, ring-forming atoms; a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24, ring-forming atoms; and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 8, ring-forming carbon atoms and a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, ring-forming carbon atoms.

[0099] Among them, two adjacent ones selected from R12~R21 and R22~R31 that are not single bonds bonded to formula (1) each independently represent a hydrogen atom, a deuterium atom, or the above-mentioned substituents, or are bonded to each other to form a ring structure. That is, the two adjacent ones do not form a ring structure but are independently represented as a hydrogen atom, a deuterium atom or the above-mentioned substituents, or the two adjacent ones are bonded to each other to form a ring structure. In one embodiment of the present invention, R12~R21 and R22~R31 that are not single bonds bonded to formula (1) are all hydrogen atoms, and in another embodiment, R12~R21 and R22~R31 that are not single bonds bonded to formula (1) are all deuterium atoms.

[0100] X2 is oxygen or sulfur atom. In one embodiment of the present invention, X2 is oxygen atom, in another embodiment, X2 is sulfur atom. X3 is oxygen or sulfur atom. In one embodiment of the present invention, X3 is oxygen atom, in another embodiment, X3 is sulfur atom.

[0101] In one embodiment of the present invention, two adjacent substituents R9 and R10 do not form a ring structure, R32 and R33 are independently represented by a substituted or unsubstituted aromatic group having 6 to 30, preferably 6 to 18, ring carbon atoms; and a substituted or unsubstituted heteroaromatic group having 5 to 30, preferably 5 to 24, ring atoms, and the details of the substituents R1 to R4, R5 to R7, R8 to R9, R11, X1, L1 to L2 and Cy1 to Cy2 are the same as the details of the corresponding substituents described in formula (1).

[0102] In another embodiment of the present invention, two adjacent substituents R9 and R10 are bonded to each other to form a ring structure, and R34 to R37 are independently hydrogen atoms, deuterium atoms, or substituents selected from halogen atoms; cyano groups; nitro groups; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, preferably 1 to 8 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 30 ring carbon atoms, preferably 3 to 8 ring carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms; substituted or unsubstituted aryl groups having 7 to 36 ring carbon atoms, preferably 7 to 2 The group consisting of an aralkyl group having 0; a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24, ring atoms; a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24 ring atoms; and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 8, carbon atoms and a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms.

[0103] Wherein, two adjacent R34 to R37 independently represent hydrogen atoms, deuterium atoms, or the above substituents, or are bonded to each other to form a ring structure. In one embodiment of the present invention, all of R34 to R37 are substituents. The substituents are preferably hydrogen atoms or deuterium atoms.

[0104] When Cy1 to Cy2 are not represented by the formula (A1) or (B1), they are represented by the following formula (F1).

[0105] [Chemistry 8]

[0106]

[0107] In formula (F1),

[0108] R38 to R42 are each independently a hydrogen atom, a deuterium atom, or a substituent selected from a halogen atom; a cyano group; a nitro group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 8 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 8 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 36 ring carbon atoms, preferably 7 to 20 ring carbon atoms; a substituted or unsubstituted The group consisting of a heteroaryl group having 5 to 30, preferably 5 to 24 ring carbon atoms; a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 24 ring carbon atoms; and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 8 ring carbon atoms and a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms.

[0109] Wherein, two adjacent groups selected from R38 to R42 independently represent hydrogen atoms, deuterium atoms, or the above-mentioned substituents, or are bonded to each other to form a ring structure. That is, the two adjacent groups do not form a ring structure but are independently represented by hydrogen atoms, deuterium atoms or the above-mentioned substituents, or the two adjacent groups are bonded to each other to form a ring structure. In one embodiment of the present invention, two adjacent groups of R38 to R42 are independently the above-mentioned substituents, and in another embodiment of the present invention, at least one group of two adjacent groups of R38 to R42 form a ring structure.

[0110] Among them, at least one group of two adjacent ones of R38 to R42 form a ring structure, and the details of the ring structure are the same as the details of the corresponding ring structure described in the above formula (1).

[0111] Compound (1) is represented by the following formulae (4) to (16).

[0112] [Chemistry 9]

[0113]

[0114] [Chemistry 10]

[0115]

[0116] [Chemistry 11]

[0117]

[0118] [Chemistry 12]

[0119]

[0120] [Chemistry 13]

[0121]

[0122] [Chemistry 14]

[0123]

[0124] [Chemistry 15]

[0125]

[0126] [Chemistry 16]

[0127]

[0128] [Chemistry 17]

[0129]

[0130] [Chemistry 18]

[0131]

[0132] [Chemistry 19]

[0133]

[0134] [Chemistry 20]

[0135]

[0136] In formulas (4) to (16),

[0137] The details of R43 to R52 and R53 to R62 are the same as those described for R12 to R21 and R22 to R31 in the above formulas (1) to (3). The details of X4 to X5 are the same as those described for X2 to X3 in the above formulas (1) to (3).

[0138] Specific examples of the compound (1) of the present invention are shown below, but the invention is not limited thereto.

[0139] [Chemistry 21]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] The method for producing the compound (1) is not particularly limited, and a person skilled in the art can easily produce it according to the method described in the following examples or by referring to a known synthesis method.

[0154] Description of OLED device structure

[0155] The device structure of the present invention comprises an anode, a cathode, and a light-emitting layer formed between the anode and the cathode, wherein the light-emitting layer comprises the compound (1) as a fluorescent dopant and at least one host material. A hole transport unit is also arranged between the anode and the light-emitting layer, and an electron transport unit is arranged between the light-emitting layer and the cathode.

[0156] The light-emitting layer can be a single light-emitting unit or a layer of multiple light-emitting units. The compound (1) can be a fluorescent light-emitting dopant in a fluorescent light-emitting layer in a single-color device with a fluorescent light-emitting mechanism, a fluorescent-phosphorescent mixed white light device, a stacked device with multiple light-emitting units, or a tandem device with multiple light-emitting units.

[0157] In a device having stacked units, each light-emitting unit can independently emit light of different or same color, for example, anode / (hole injection layer / )hole transport layer / red phosphorescent light-emitting layer / green phosphorescent light-emitting layer / spacer layer / blue fluorescent light-emitting layer containing compound (1) / electron transport layer / electron injection layer / cathode.

[0158] Figure 1Provided is a schematic diagram of an OLED device structure 300. Taking the device structure 300 as an example, it includes a substrate 31, an anode 32 prepared on the substrate 31, a light-emitting unit 35 formed on the anode 32, and a cathode 38 on the light-emitting unit 35. A hole transport unit 33 composed of a first hole transport layer 33a and a second hole transport layer 33b and an electron blocking layer 34 formed on the hole transport unit 33 are formed in sequence between the anode 32 and the light-emitting unit 35. An electron transport unit 36 ​​composed of a first electron transport layer 36a and a second electron transport layer 36b and an electron injection layer 37 formed on the electron transport unit 36 ​​are formed in sequence between the light-emitting unit 35 and the cathode 38. The polycyclic compound (1) is used as a fluorescent dopant in the light-emitting layer 35.

[0159] Materials used in OLED devices

[0160] The content WW of the polycyclic compound (1) in the device material of the present invention is not particularly limited, and is selected within the range of WW ≤ 50 mass %, preferably WW ≤ 10 mass %.

[0161] Example

[0162] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[0163] Intermediate Synthesis Example 1 Synthesis of Intermediate 1-e

[0164]

[0165] Intermediate 1-e was synthesized by the same procedure as described in CN115611937A.

[0166] Under sufficient nitrogen replacement, 1 mmol of the raw materials 1-a, 1 mmol of 1-b, 1.5 g of tris(dibenzylideneacetone)dipalladium(0), 1.0 g of bis(diphenylphosphine)-1,1'-binaphthyl, sodium tert-butyl alcohol and toluene solution were added to the reaction bottle, and then refluxed for 6 hours. After the reaction was completed, it was cooled to room temperature and purified by silica gel column.

[0167] Then, the obtained solid product 1-c was added to a glass bottle containing 1 mmol 1-d, and then bis(tri-tert-butylphosphine)palladium(0), sodium tert-butyl alcohol and toluene solution were added, and the nitrogen was fully replaced and refluxed for 6 hours. After the reaction was completed and cooled to room temperature, it was refined and purified by a silica gel column to obtain intermediate 1-e.

[0168] Intermediate Synthesis Example 2 Synthesis of Intermediate 1-i

[0169]

[0170] Under nitrogen atmosphere, 1 mmol of raw materials 1-f, 1 mmol of 1-g, 1.18 g of tris(dibenzylideneacetone)dipalladium(0), 0.85 g of bis(diphenylphosphine)-1,1'-binaphthyl, sodium tert-butyl alcohol and toluene solution were added to a reaction flask. Then, the reaction was refluxed for 8 hours, and after cooling to room temperature, the reaction was purified by silica gel column.

[0171] Under nitrogen atmosphere, the obtained solid product 1-h, bis(tri-tert-butylphosphine)palladium(0), sodium tert-butyl alcoholate and toluene solution were added to a glass bottle containing 1 mmol 1-d, and then refluxed for 8 hours. After the reaction was completed and cooled to room temperature, it was refined and purified by silica gel column to obtain intermediate 1-i.

[0172] Intermediate Synthesis Example 3 Synthesis of Intermediate 1-1

[0173]

[0174] Under nitrogen atmosphere, 1 mmol of the raw materials 1-j, 1 mmol of 1-g, 1.12 g of tris(dibenzylideneacetone)dipalladium(0), 0.8 g of bis(diphenylphosphine)-1,1'-binaphthyl, sodium tert-butyl alcohol and toluene solution were refluxed for 6 hours, cooled to room temperature and purified by silica gel column.

[0175] Under a nitrogen atmosphere, the obtained solid product 1-k was added to a glass bottle containing 1 mmol of 1-d, and bis(tri-tert-butylphosphine)palladium(0), sodium tert-butyl alcoholate and toluene solution were added to carry out reflux reaction for 8 hours. After the reaction was completed and cooled to room temperature, it was refined and purified by a silica gel column to obtain intermediate 1-1.

[0176] Intermediate Synthesis Example 4 Synthesis of Intermediate 1-m

[0177]

[0178] Intermediate 1-m was synthesized by using the same procedure as Intermediate 1-e except that Intermediate 1-b was replaced by 1-g.

[0179] Intermediate Synthesis Example 5 Synthesis of Intermediate 1-o

[0180]

[0181] Intermediate 1-o was synthesized by using the same procedure as for intermediate 1-e except that intermediate 1-a was replaced by 1-n.

[0182] Intermediate Synthesis Example 6 Synthesis of Intermediate 1-q

[0183]

[0184] Intermediate 1-q was synthesized using the same procedure as for Intermediate 1-e except that Intermediates 1-a and 1-b were replaced by 1-p and 1-g.

[0185] Intermediate Synthesis Example 7 Synthesis of Intermediate 1-s

[0186]

[0187] Intermediate 1-s was synthesized by using the same procedure as for intermediate 1-e except that intermediates 1-a and 1-b were replaced by 1-r and 1-g.

[0188] Intermediate Synthesis Example 8 Synthesis of Intermediate 2-c

[0189]

[0190] Under nitrogen replacement, 1 mmol 2-a and 1 mmol 2-b were added to a reaction bottle containing 2.5 g tris(dibenzylideneacetone)dipalladium(0), 25 g sodium tert-butyl alcohol, 1.6 g bis(diphenylphosphine)-1,1'-binaphthyl and 550 ml toluene, and the mixture was stirred and refluxed for 6 hours. After cooling to room temperature, the mixture was purified by silica gel column to obtain intermediate 2-c.

[0191] Intermediate Synthesis Example 9 Synthesis of Intermediate 2-e

[0192]

[0193] After nitrogen is fully replaced, 1 mmol 2-a and 1 mmol 2-d are added to a reaction bottle containing 2.1 g tris(dibenzylideneacetone)dipalladium(0), 23 g sodium tert-butyl alcohol, 1.5 g bis(diphenylphosphine)-1,1'-binaphthyl and 550 ml toluene, and the mixture is stirred and refluxed for 7 hours. After cooling to room temperature, the mixture is purified by silica gel column to obtain intermediate 2-e.

[0194] Intermediate Synthesis Example 10 Synthesis of Intermediate 2-g

[0195]

[0196] Intermediate 2-g was synthesized by the same procedure as for Intermediate 2-c except that Intermediate 2-b was replaced by 2-f.

[0197] Intermediate Synthesis Example 11 Synthesis of Intermediate 2-i

[0198]

[0199] Intermediate 2-i was synthesized using the same procedure as Intermediate 2-c except that Intermediates 2-b and 2-a were substituted for 2-h and 2-f.

[0200] Intermediate Synthesis Example 12 Synthesis of Intermediate 2-j

[0201]

[0202] Intermediate 2-j was synthesized by the same procedure as for Intermediate 2-c except that Intermediate 2-a was substituted for 2-h.

[0203] Intermediate Synthesis Example 13 Synthesis of Intermediate 2-1

[0204]

[0205] Intermediate 2-1 was synthesized using the same procedure as for Intermediate 2-c except that Intermediate 2-a was substituted for 2-k.

[0206] Intermediate Synthesis Example 14 Synthesis of Intermediate 2-m

[0207]

[0208] Intermediate 2-m was synthesized using the same procedure as for Intermediate 2-c except that Intermediates 2-a and 2-b were substituted for 2-k and 2-f.

[0209] Synthesis Example 1 Synthesis of Compound 1

[0210]

[0211] After nitrogen is fully replaced, 1 mmol of intermediate 1-e and 1 mmol of 2-c are added to the reaction flask, and 0.9 g of bis(tri-tert-butylphosphine)palladium(0), 5 g of sodium tert-butoxide, and 500 ml of toluene solution are added, and then heated to reflux for 6 hours. After the reaction is completed, it is cooled to room temperature and purified by silica gel column to obtain intermediate m-1.

[0212] Add intermediate m-1 to a reaction bottle containing 400 ml of tert-butylbenzene solution, and then drop 55 ml of 1.7 M tert-butyl lithium pentane solution at -78 ° C. Heat to 60 ° C and stir for 4 hours. Blow nitrogen at 60 ° C to completely drive off pentane. Cool to -78 ° C, drop 20 ml of boron tribromide, heat to room temperature, and stir for 5 hours. Cool to 0 ° C, drop 10 ml of N, N-diisopropylethylamine. Heat to 120 ° C and stir the reaction for 12 hours. After cooling to room temperature, separate the organic layer and purify with a silica gel column to obtain the product.

[0213] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1180.35, m / e=1179, and was compound 1.

[0214] Synthesis Example 2 Synthesis of Compound 2

[0215]

[0216] The product was synthesized using the same procedure as compound 1 except that intermediate 2-c was substituted for 2-e.

[0217] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1180.35, m / e=1179, and was compound 2.

[0218] Synthesis Example 3 Synthesis of Compound 3

[0219]

[0220] The product was synthesized using the same procedure as compound 1 except that intermediate 1-e was substituted for 1-i.

[0221] The result of mass spectrometry analysis of the obtained product was: relative molecular weight 1172.371, m / e=1171, and it was compound 3.

[0222] Synthesis Example 4 Synthesis of Compound 4

[0223]

[0224] The product was synthesized by the same procedure as compound 1 except that intermediate 2-c was substituted for 2-g.

[0225] The result of mass spectrometry analysis of the obtained product was: relative molecular weight 1204.372, m / e=1203, and it was compound 4.

[0226] Synthesis Example 5 Synthesis of Compound 5

[0227]

[0228] The product was synthesized using the same procedure as for compound 1, except that intermediates 2-c and 1-e were substituted for 2-g and 1-1.

[0229] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1182.366, m / e=1181, and was compound 5.

[0230] Synthesis Example 6 Synthesis of Compound 6

[0231]

[0232] The same operation as compound 1 was used to synthesize the product except that intermediates 1-e and 2-c were substituted for 1-m and 2-i. The mass spectrometry analysis of the obtained product showed that the relative molecular weight was 1182.366, m / e=1181, and the product was compound 6.

[0233] Synthesis Example 7 Synthesis of Compound 7

[0234]

[0235] The product was synthesized by using the same operation as compound 1 except that intermediates 1-e and 2-c were substituted for 1-m and 2-j. The obtained product was analyzed by mass spectrometry: relative molecular weight 1158.345, m / e=1157, which was compound 7.

[0236] Synthesis Example 8 Synthesis of Compound 8

[0237]

[0238] The product was synthesized using the same procedure as compound 1 except that intermediate 1-e was substituted for 1-o.

[0239] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1206.387, m / e=1205, and was compound 8.

[0240] Synthesis Example 9 Synthesis of Compound 9

[0241]

[0242] The product was synthesized by the same procedure as compound 1 except that intermediate 1-e was substituted for 1-q.

[0243] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1188.286, m / e=1187, and was compound 9.

[0244] Synthesis Example 10 Synthesis of Compound 10

[0245]

[0246] The same operation as compound 1 was used to synthesize the product except that intermediates 1-e and 2-c were substituted for 1-s and 2-1. The mass spectrometry analysis of the obtained product showed that the relative molecular weight was 1157.441, m / e=1156, and the product was compound 10.

[0247] Synthesis Example 11 Synthesis of Compound 11

[0248]

[0249] The product was synthesized using the same procedure as compound 1 except that the intermediates were replaced with 1-s and 2-m.

[0250] The obtained product was subjected to mass spectrometry analysis: relative molecular weight 1181.463, m / e=1180, and was compound 11.

[0251] Example 1

[0252] The first hole transport layer 33a is composed of: HATCN (3wt%): HT1; the second hole transport layer 33b is composed of: HT1; the electron blocking layer 34 is composed of: HT2; the light-emitting layer 35 is composed of: compound BH1 (98wt%): compound 1 (2wt%); the first electron transport layer 36a is composed of: ET1; the second electron transport layer 16b is composed of: ET1:LiQ; the electron injection layer 37 is composed of: Yb; the cathode layer 18 is composed of: Mg:Ag (1:9) alloy; the light extraction layer: HT1.

[0253] Material structure used in the device

[0254]

[0255] Characterization of device performance

[0256] At 10mA / cm 2 The efficiency was tested under the following conditions and the results are recorded in Table 1.

[0257] At 20mA / cm 2 The brightness decays to 95% of the initial value, which is defined as LT95. The results are shown in Table 1 below.

[0258] Embodiments 2 to 11

[0259] Compound 1 was replaced by compounds 2 to 11, which acted as fluorescent dopants in the light-emitting layer 35 respectively. Devices 2 to 11 were manufactured in the same manner as in Example 1, and the device performance was tested. The results are shown in Table 1.

[0260] Comparative Examples 1 to 7

[0261] Compound 1 was replaced with "Comparative Compound 1" (compound recorded in reference patent document 1), or "Comparative Compound 2" (compound recorded in reference patent document 2), or "Comparative Compound 3" (compound recorded in reference patent document 3), or "Comparative Compound 4" (compound recorded in reference patent document 4), or "Comparative Compound 5" (compound recorded in reference patent document 5), or "Comparative Compound 6" (compound recorded in reference patent document 6), or "Comparative Compound 7" (compound recorded in reference patent document 7), or "Comparative Compound 8" (compound recorded in reference patent document 8), or "Comparative Compound 9" (compound recorded in reference patent document 9) as the material of the light-emitting layer 35. The same device preparation process and measurement conditions were used, and the results are shown in Table 1.

[0262] Materials used in Comparative Examples 1 to 9

[0263]

[0264] It should be particularly pointed out that compounds 1 to 11 of the present invention simultaneously meet two important conditions, namely, molecular structural element Q-1: the electron-rich nitrogen atom and the electron-deficient boron atom in the para position constitute a multi-resonance excited state luminescence plane; molecular element Q-2: the triplet π electron density regulation center with super one-dimensional expansion is bonded to the electron-rich nitrogen atom.

[0265] "Comparative compounds 1 to 9" do not satisfy structural element Q-2, and "Comparative compounds 8 to 9" do not satisfy structural element Q-1.

[0266] [Table 1]

[0267]

[0268]

[0269] Referring to Table 1, Examples 1 to 11 exhibited the functions of long life and high efficiency.

[0270] Without being bound by theory, it is believed that compounds 1 to 11 according to the examples form a multi-resonance luminescent property after introducing the molecular element Q-1, which is beneficial to improving the exciton utilization rate of the fluorescent luminescent dopant, while comparative examples 8 to 9 do not have the molecular element Q-1 and thus have low efficiency. Comparative example 8 is a host material with a TTA effect, and comparative example 9 is a traditional fluorescent host material; without being bound by theory, it is believed that compounds 1 to 11 according to the examples introduce the molecular element Q-2, which is beneficial to improving the molecular orientation of the fluorescent dopant, the resistance to triplet excitons and electron carriers, shortening the residence time of excitons and electron carriers on the luminescent surface due to the more extended electron density adjustment center, and enhancing the resistance to decomposition of blue light. Based on the synergistic effect of the above molecular elements Q-1 & Q-2, the polycyclic compound of the present invention has the function of improving the efficiency and life of the blue light device.

[0271] In order to illustrate the technical advantages of the present invention and further prove the synergistic effect of the molecular elements Q-1 and Q-2, the present inventors attempted to conduct a profound and comprehensive analysis and comparison from multiple theoretical dimensions.

[0272] [Dipole moment, HOMO energy level, LUMO energy level]

[0273] Dipole moment of a molecule Given by the following formula:

[0274]

[0275] Among them, q i and r i is the local charge and position of atom i in the molecule.

[0276] The dipole moment was determined by the semi-empirical molecular orbital method. The molecular geometry was optimized by Gaussian09 using the hybrid functional B3LYP and 6-31g(d) basis set to determine the HOMO and LUMO energy levels of the molecular structure. The dipole moment, HOMO and LUMO energy levels are recorded in Table 2.

[0277] [Fluorescence radiation rate constant, quantum efficiency]

[0278] The fluorescence radiation rate constant reflects the light radiation rate of the fluorescent small molecule from the fluorescence excited state to the ground state. If the fluorescence radiation rate constant is large, the non-radiative rate constant will be weakened and the fluorescence luminescence will be improved, and the quantum efficiency will also be improved. The fluorescence radiation rate constant and quantum efficiency were measured by FluoroMax-4 transient fluorescence spectrometer and recorded in Table 2.

[0279] Thin film preparation conditions: 100 nm organic thin film was prepared by evaporation and tested in a nitrogen atmosphere.

[0280] [Photoluminescence intensity test]

[0281] A 100 nm thick material of the object to be tested was prepared on a substrate, and then irradiated with 365 nm ultraviolet light to cause photoluminescence of the object to be tested to generate light intensity. The time from the initial photoluminescence intensity decaying to 50% was defined as LT50. The results are recorded in Table 2.

[0282] [Electronic tolerance and dissociation energy]

[0283] According to the records in the reference literature (e.g. Adv. Mater. 2013, 25, 2114-2129), organic matter is very sensitive to electron carriers. Once the electron carriers are in excess, the weaker CN bonds tend to break, resulting in complex chemical degradation of the organic matter. The energy BDE- of the lowest chemical bond breakage of the blue light material in the electron carrier environment can be observed by Gaussian09 software, and the results are recorded in Table 2.

[0284] [Table 2]

[0285]

[0286] Table 2 shows the dipole moment, HOMO and LUMO energy levels of compounds 1 / 8 / 11 and comparative compounds 4 / 5. The values ​​are suitable for use as fluorescent dopants for blue light devices. Referring to Table 2, due to the synergistic effect of molecular elements Q-1 and Q-2, compounds 1 / 8 have higher quantum efficiency PLQY than comparative compound 5, and compound 11 has higher photoinduced decay lifetime LT50 than comparative compound 4, and greater electron dissociation resistance energy BDE-.

[0287] Although the present application is disclosed as above with preferred embodiments, it is not intended to limit the claims. Any technical personnel in this field may make several possible changes and modifications without departing from the concept of the present application. Therefore, the scope of protection of the present application shall be based on the scope defined by the claims of the present application.

Claims

1. A polycyclic compound, the polycyclic compound being represented by the following formula (1): In formula (1), L1 is a single bond or L11, L11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; L2 is a single bond or L22, L22 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; X1 is an oxygen atom, a sulfur atom, or a selenium atom; R1 to R4, R5 to R7 and R8 to R11 each independently represent a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, in, Two adjacent ones of R1 to R4, R5 to R7 and R8 to R11 independently represent a hydrogen atom, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure; Cy1 to Cy2 are the same or different from each other, and at least one of Cy1 to Cy2 is the following formula (A1) or (B1), In the above formulas (A1) and (B1), One of R12 to R21 and R22 to R31 is a single bond bonded to the above formula (1); R12 to R21 and R22 to R31 which are not single bonds to the above formula (1) are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Among them, two adjacent ones of R12 to R21 and R22 to R31 that are not single bonds to the above formula (1) each independently represent a hydrogen atom, deuterium, or the above substituent, or are bonded to each other to form a ring structure; X2 to X3 are oxygen atoms or sulfur atoms.

2. The polycyclic compound according to claim 1, wherein when two adjacent substituents R9 and R10 do not form a ring structure, the polycyclic compound is represented by the following formula (2): In formula (2), R32 and R33 are independently substituted or unsubstituted aryl having 6 to 30 ring carbon atoms and substituted or unsubstituted heteroaryl having 5 to 30 ring atoms; R1 to R4, R5 to R7, R8 to R9, R11, X1, L1 to L2 and Cy1 to Cy2 are as defined in formula (1).

3. The polycyclic compound according to claim 1, wherein two adjacent substituents R9 and R10 are bonded to each other to form a ring structure represented by the following formula (3): In formula (3), Cy3 is represented by any of the following formulas (C1), (D1) or (E1), In formula (D1), R34 to R37 are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. in, Two adjacent ones of R34 to R37 independently represent a hydrogen atom, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure; "*" represents the bonding site.

4. The polycyclic compound according to claim 1 to 3, wherein when Cy1 to Cy2 are not of formula (A1) or (B1), they are represented by the following formula (F1): In formula (F1), R38 to R42 are each independently a hydrogen atom, a deuterium atom, or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a disubstituted amino group having a substituent selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, in, Two adjacent ones of R34 to R37 independently represent a hydrogen atom, deuterium, or the above-mentioned substituents, or are bonded to each other to form a ring structure; "*" represents the bonding site.

5. The polycyclic compound according to claim 1 to 4, which is represented by the following formulas (4) to (16): In formulas (4) to (16), The details of R43 to R52 and R53 to R62 are the same as the details described in claims 1 to 4 for R12 to R21 and R22 to R31; The details of X4 to X5 are the same as the details described in claims 1 to 4 with respect to X2 to X3.

6. The polycyclic compound according to claims 1 to 5, wherein In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L11, the arylene group having 6 to 30 ring carbon atoms is selected from the group consisting of phenylene, biphenylene and naphthylene; In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L22, the arylene group having 6 to 30 ring carbon atoms is selected from the group consisting of phenylene, biphenylene and naphthylene.

7. The polycyclic compound according to claims 1 to 6, which is represented by any one of the following formulae: 8 . A material for an organic electroluminescent device, comprising the compound according to claim 1 .

9. An organic electroluminescent device, comprising a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer comprises the polycyclic compound described in any one of claims 1 to 7 as a dopant for the light-emitting layer, and at least one main material, wherein the main material is one of an anthracene compound, a pyrene compound, or a fluorene compound.

10. The organic electroluminescent device according to claim 9, characterized in that: A hole transport unit is included between the anode and the light-emitting layer, and an electron transport unit is included between the light-emitting layer and the cathode.

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