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US-12619144-B2 - Positive photosensitive resin composition

US12619144B2US 12619144 B2US12619144 B2US 12619144B2US-12619144-B2

Abstract

A positive photosensitive resin composition includes a polymer resin, a quinonediazide compound, and a solvent. The polymer resin includes (i) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula 1, ii) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula 2, and iii) 0 to 20 wt. % of a polyimide precursor having a structural unit represented by Formula 3. The quinonediazide compound is included in an amount of 5 to 50 parts by weight per 100 parts by weight of the polymer resin. The solvent is included in an amount of 100 to 2,000 parts by weight per 100 parts by weight of the polymer resin.

Inventors

  • Hyoc Min YOUN
  • TAI HOON YEO
  • Gi Seon LEE
  • Bong Hee Kim
  • Dong Myung Kim

Assignees

  • DONGJIN SEMICHEM CO., LTD.

Dates

Publication Date
20260505
Application Date
20220630
Priority Date
20191231

Claims (12)

  1. 1 . A positive photosensitive resin composition comprising: a polymer resin comprising i) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula 1, ii) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula 2, and iii) 0 to 20 wt. % of a polyimide precursor having a structural unit represented by Formula 3; 5 to 50 parts by weight of a quinonediazide compound per 100 parts by weight of the polymer resin; and 100 to 2,000 parts by weight of a solvent per 100 parts by weight of the polymer resin, wherein R 1 and R 2 are each independently an organic group having 5 to 30 carbon atoms, wherein in the organic group, hydrogen can be substituted with a hydroxyl group (OH), methyl, or fluorine, the methylene group can be substituted with oxygen or nitrogen, and R 3 is a substituent derived from epoxy.
  2. 2 . The positive photosensitive resin composition of claim 1 , wherein R 3 is a substituent represented by Formula 4: wherein R 4 is a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, wherein the hydrogen atom of the alkyl group can be substituted with 1 to 3 fluorine atoms or hydroxyl groups, and the methylene group can be substituted with an alkenyl group, oxygen, nitrogen, ester (COO), or carbonyl (C═O).
  3. 3 . The positive photosensitive resin composition of claim 1 , wherein R 3 is derived from a compound selected from the group consisting of epoxycyclohexylmethylmethacrylate, 1,2-epoxy-4-vinylcyclohexene, 3,4-(epoxycyclohexene) methyl-3′,4′-epoxycyclohexylcarboxylate, and 3,4-epoxycyclo hexylmethyl-3′,4′-epoxycyclohexenecarboxylate modified epsilon-caprolactone.
  4. 4 . The positive photosensitive resin composition of claim 1 , wherein each of the polyimide precursor having a structural unit represented by Formula 1, the polyimide precursor having a structural unit represented by Formula 2, and the polyimide precursor having a structural unit represented by Formula 3 has a weight average molecular weight in a range of 3,500 to 20,000.
  5. 5 . The positive photosensitive resin composition of claim 1 , wherein the polymer resin contains 50 to 95 wt. % of a polyimide having a structural unit represented by Formula 2.
  6. 6 . The positive photosensitive resin composition of claim 1 , wherein the quinonediazide compound is obtained by reacting a phenol compound selected from the group consisting of compounds represented by Formulas 4-1 to 4-3 and a naphthoquinonediazidesulfonic halogen compound: wherein R 31 to R 36 are each independently hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms, R 37 and R 38 are each independently hydrogen, halogen, or an alkyl group having 1 to 4 carbon atoms, and R 39 is hydrogen or an alkyl group having 1 to 4 carbon atoms.
  7. 7 . The positive photosensitive resin composition of claim 1 , wherein the solvent is selected from the group consisting of gamma butyrolactone (GBL), N-methylpyrrolidone (NMP), propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl-3-methoxypropionate (MMP), propylene glycol monomethyl ether (PGME), and mixtures thereof.
  8. 8 . The positive photosensitive resin composition of claim 1 , further comprising an additive selected from the group consisting of a thermal crosslinking agent, a thermal acid generator, a UV absorber, and a mixture thereof.
  9. 9 . The positive photosensitive resin composition of claim 8 , wherein the thermal crosslinking agent comprises a functional group represented by Formula 5: wherein A is Formula a, wherein n is an integer in a range of 1 to 6, and Ra is an alkyl having 1 to 3 carbon atoms:
  10. 10 . The positive photosensitive resin composition of claim 8 , wherein the thermal crosslinking agent is selected from the group consisting of compounds represented by Formulas 5-1 to 5-4: wherein A is Formula a, wherein n is an integer in a range of 1 to 6, and Ra is an alkyl having 1 to 3 carbon atoms:
  11. 11 . The positive photosensitive resin composition of claim 8 , wherein the thermal crosslinking agent is contained in an amount of 10 to 50 parts by weight per 100 parts by weight of the polymer resin.
  12. 12 . A display device comprising a driving circuit, a planarization layer, a first electrode, an insulating layer, a light emitting layer, and a second electrode that are formed on a substrate, wherein either one or both of the planarization layer and the insulating layer are made from the positive photosensitive resin composition of claim 1 .

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a Continuation of International Application No. PCT/KR2020/019343, filed on Dec. 29, 2020, which claims priority to Korean Application No. 10-2019-0179822, filed on Dec. 31, 2019, and Korean Application No. 10-2020-0185639, filed on Dec. 29, 2020. The aforementioned applications are incorporated herein by reference in their entireties. TECHNICAL FIELD The present invention relates to a positive photosensitive resin composition, and more particularly, to a positive photosensitive resin composition used in a display device. RELATED ART In the recent market, organic light emitting diodes (OLEDs), especially active matrix OLED (AMOLED), are in the spotlight for several reasons among display devices. Typically, an OLED device includes an organic insulating film, and a polyimide photosensitive resin composition is generally used to form the organic insulating film. Among polyimide precursors used in conventional polyimide photosensitive resin compositions, the technology of substituting alkyls for polyamic esters was used. However, the polyamic esters substituted with alkyls are difficult in solubility control and have low sensitivity. Therefore, measures for improvement of the polyamic esters were urgently requested. SUMMARY Accordingly, the objective of the present invention is to provide a positive photosensitive resin composition that can be easily controlled in solubility and which has significantly improved sensitivity. In order to achieve the above objective, the present invention provides a positive photosensitive resin composition including: a polymer resin including i) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula (1), ii) 5 to 95 wt. % of a polyimide precursor having a structural unit represented by Formula (2), and iii) 0 to 20 wt. % of a polyimide precursor having a structural unit represented by Formula (3); 5 to 50 parts by weight of a quinonediazide compound per 100 parts by weight of the polymer resin; and 100 to 2,000 parts by weight of a solvent per 100 parts by weight of the polymer resin. In Formulas 1 to 3, R1 and R2 are each independently an organic group having 5 to 30 carbon atoms. In the organic group, hydrogen may be substituted with a hydroxyl group (OH), methyl, or fluorine. The methylene group may be substituted with oxygen or nitrogen. R3 is a substituent derived from epoxy. The present invention also provides a display device including a driving circuit, a planarization layer, a first electrode, an insulating layer, a light emitting layer, and a second electrode on a substrate, in which at least one of the planarization layer and the insulating layer is formed from the positive photosensitive resin composition. The positive photosensitive resin composition according to the present invention is easily controlled in solubility, improves sensitivity, chemical resistance, adhesion, etc., when forming a pattern of a display device such as OLED, and inhibits generation of scum and cracks. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a view showing that a pattern film is formed on an indium tin oxide (ITO) substrate with a pattern formed thereon, and electroluminescent lighting (EL) is deposited, according to an embodiment of the present invention. DETAILED DESCRIPTION Hereinafter, the present invention will be described in detail. In the present specification, “*” means a moiety connected to the same or different atom or chemical formula. The positive photosensitive resin composition according to the present invention contains a polymer resin, a quinonediazide compound, and a solvent. The polymer resin used in the present invention is polymerized to form a polyimide film. The polymer resin may contain: 5 to 95 wt. %, specifically 10 to 90 wt. % of a polyimide precursor having a structural unit represented by Formula (1); 5 to 95 wt. %, specifically 50 to 90 wt. % of polyimide having a structural unit represented by Formula (2); and 0 to 20 wt. %, specifically 0 to 15 wt. %, of a polyimide precursor having a structural unit represented by Formula (3). In Formulas 1 to 3, R1 and R2 may each independently be an organic group having 5 to 30 carbon atoms, specifically, an organic group having 5 to 20 carbon atoms. Hydrogen in the organic group may be substituted with a hydroxyl group (OH), methyl, or fluorine, and the methylene group may be substituted with oxygen or nitrogen. R3 is a substituent derived from epoxy and, more specifically, may be a substituent represented by Formula (4). In Formula 4, R4 is a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, in which a hydrogen atom of the alkyl group may be substituted with 1 to 3 fluorine or hydroxyl groups, and the methylene group may be substituted with an alkenyl group, oxygen, nitrogen, ester (COO), or carbonyl (C═O). As the substituent represented by Formula 4, R3 is specifically a compound derived from a compound selec